JournalTOCs

Molbank
Journal Prestige (SJR): 0.12

Number of Followers: 0

This is an Open Access Journal

Open Access journal
ISSN (Print) 1422-8599
Published by MDPI

[84 journals]

Molbank, Vol. 2022, Article M1392: Styryl Hemicyanine Dye
(E)-3-Methyl-2-(4-thiomorpholinostyryl)benzo[d]thiazol-3-ium Iodide for
Nucleic Acids and Cell Nucleoli Visualization
- Authors: Aleksey A. Vasilev, Marina Miteva, Nikolay Ishkitiev, Maria Dragneva, Lora Topalova, Meglena I. Kandinska
  Abstract: (E)-3-Methyl-2-(4-thiomorpholinostyryl)benzo[d]thiazol-3-ium iodide 1 was prepared by a convenient and reliable reaction procedure. The slight molar excess of the starting benzaldehyde and the mixture of ethanol: ethyl acetate in the ratio 3:1 as a solvent afforded a pure reaction product. The photophysical properties of the dye in a TE buffer in the absence and presence of double-stranded DNA (dsDNA) were elucidated. The low intrinsic fluorescence of 1 in TE buffer is followed by an increase in the fluorescence after dsDNA binding. The dye is nontoxic for stem cells from apical papilla and the most concentrated fluorescence is detected in the cell nucleoli.
  Citation: Molbank
  PubDate: 2022-06-20
  DOI: 10.3390/M1392
  Issue No: Vol. 2022, No. 2 (2022)
Molbank, Vol. 2022, Article M1391: Fosbergenone:
- Authors: Joy Ebenezer Rajakulendran, Emmanuel T. Oluwabusola, Rainer Ebel, Marcel Jaspars
  Abstract: A new ent-halimane diterpenoid, fosbergenone (1) was isolated from the foliar bud exudate of Gardenia fosbergii. The structure of 1 was elucidated based on spectroscopic data including IR, 1D and 2D NMR, as well as high-resolution mass spectrometry.
  Citation: Molbank
  PubDate: 2022-06-19
  DOI: 10.3390/M1391
  Issue No: Vol. 2022, No. 2 (2022)
Molbank, Vol. 2022, Article M1390: Bis(3-butylamino-4-nitro)piperazine
- Authors: M. John Plater, David P. B. Bulloch, William T. A. Harrison
  Abstract: 2,4-Difluoronitrobenzene is treated sequentially with butylamine and then piperazine to prepare a building block for forming a crystalline lattice by non-covalent interactions. A single crystal X-ray structure determination was performed.
  Citation: Molbank
  PubDate: 2022-06-18
  DOI: 10.3390/M1390
  Issue No: Vol. 2022, No. 2 (2022)
Molbank, Vol. 2022, Article M1389:
N-[3-(Chloromethyl)-1,2-benzisoxazol-5-yl]acetamide
- Authors: Evgeniy N. Khodot, Oleg A. Rakitin
  Abstract: Functionally substituted 1,2-benzisoxazoles are very important and promising heterocycles with various pharmacological activities. Benzoxazoles containing reactive 3-chloromethyl and 5-amino groups are practically unexplored derivatives in this series. In this communication, the simple method for the synthesis of N-[3-(chloromethyl)-1,2-benzisoxazol-5-yl]acetamide which is an interesting precursor for the preparation of a series of 3,5-disubstituted benzoxazoles was described. The structure of the synthesized compound was established by elemental analysis, high-resolution mass spectrometry, 1H, 13C NMR and IR spectroscopy, and mass spectrometry.
  Citation: Molbank
  PubDate: 2022-06-17
  DOI: 10.3390/M1389
  Issue No: Vol. 2022, No. 2 (2022)
Molbank, Vol. 2022, Article M1388:
- Authors: Neil T. Mucha, Rory Waterman
  Abstract: The molecular structure of an iridium complex featuring a phenylphosphine ligand is described. The reaction of (POCOP)IrHCl (1, POCOP = 2,6-(tBu2PO)2C6H3–) with phenylphosphine gives (POCOP)IrHCl(PH2Ph) (2) under mild conditions. The structural features are consistent with a classic pseudo-octahedral iridium compound with three neutral phosphine donors. Compound 1 is unreactive at elevated temperatures and is unreactive toward excess phenylphosphine under the sampled conditions.
  Citation: Molbank
  PubDate: 2022-06-17
  DOI: 10.3390/M1388
  Issue No: Vol. 2022, No. 2 (2022)
Molbank, Vol. 2022, Article M1387: Synthesis, Spectroscopic Analysis, and
In Vitro Anticancer Evaluation of 2-(Phenylsulfonyl)-2H-1,2,3-triazole
- Authors: Angélica Salinas-Torres, Jaime Portilla, Hugo Rojas, Diana Becerra, Juan-Carlos Castillo
  Abstract: The 1,2,3-Triazole derivatives containing the sulfonyl group have proved their biological importance in medicinal chemistry and drug design. In this sense, we describe the regioselective synthesis of 2-(phenylsulfonyl)-2H-1,2,3-triazole 3 in good yield through a classical sulfonamidation reaction of 1H-1,2,3-triazole 1 with benzenesulfonyl chloride 2 in dichloromethane using a slight excess of triethylamine at 20 °C for 3 h. This procedure is distinguished by its short reaction time, high yield, excellent regioselectivity, clean reaction profile, and operational simplicity. The sulfonamide 3 was characterized by high-resolution mass spectrometry, FT–IR, UV–Vis, 1D and 2D NMR spectroscopy, and elemental analysis. The sulfonamide 3 exhibited moderate activity against UO-31 renal, SNB-75 central nervous system, HCT-116 colon, and BT-549 breast cancer cell lines, with growth inhibition percentages (GI%) ranging from 10.83% to 17.64%.
  Citation: Molbank
  PubDate: 2022-06-16
  DOI: 10.3390/M1387
  Issue No: Vol. 2022, No. 2 (2022)
Molbank, Vol. 2022, Article M1386: 3,4-Diaminopyridine-2,5-dicarbonitrile
- Authors: Timofey N. Chmovzh, Oleg A. Rakitin
  Abstract: Pyridines fused with heterocyclic rings are of great interest as both photovoltaic materials and biologically active compounds. The most convenient precursors for these compounds are pyridine-2,3-diamines. In this communication, 3,4-diaminopyridine-2,5-dicarbonitrile was synthesized by the reaction of 2,5-dibromo-3,4-diaminopyridine with copper cyanide; the best yield of the target compound was achieved by heating the reaction mixture in N,N-dimethylformamide at 120 °C for 6 h. The structure of the newly synthesized compound was established by means of elemental analysis, high resolution mass-spectrometry, 1H, 13C NMR, IR, UV spectroscopy and mass-spectrometry.
  Citation: Molbank
  PubDate: 2022-06-16
  DOI: 10.3390/M1386
  Issue No: Vol. 2022, No. 2 (2022)
Molbank, Vol. 2022, Article M1385:
(E)-7-(4-(Diphenylamino)styryl)benzo[c][1,2,5]thiadiazole-4-carbonitrile
- Authors: Timofey N. Chmovzh, Timofey A. Kudryashev, Oleg A. Rakitin
  Abstract: Donor-acceptor-donor (D-A-A) structures with 2,1,3-benzothiadiazole as an internal acceptor and the 4(7)-cyanogroup as anchor acceptor have been investigated for various photovoltaic applications such as dye-sensitized solar cells (DSSCs) and organic light emitting diodes (OLEDs). They are usually obtained by cyanation of 4(7)-bromo-2,1,3-benzothiadiazoles. In this communication, the reaction of (E)-4-(2-(7-bromobenzo[c][1,2,5]thiadiazol-4-yl)vinyl)-N,N-diphenylaniline with cyanating agents was studied and it was shown that the best yield of (E)-7-(4-(diphenylamino)styryl)benzo[c][1,2,5]thiadiazole-4-carbonitrile was achieved by heating with zinc cyanide in NMP at 120 °C in the presence of tetrakis(triphenylphosphine)palladium (0). The structure of newly synthesized compound was established by means of an elemental analysis, high resolution mass-spectrometry, 1H, 13C-NMR, IR, UV spectroscopy and mass-spectrometry.
  Citation: Molbank
  PubDate: 2022-06-15
  DOI: 10.3390/M1385
  Issue No: Vol. 2022, No. 2 (2022)
Molbank, Vol. 2022, Article M1384: A Direct Method for the Efficient
Synthesis of Hydroxyalkyl-Containing Azoxybenzenes
- Authors: Ekaterina S. Spesivaya, Ida A. Lupanova, Dzhamilya N. Konshina, Valery V. Konshin
  Abstract: Reaction of nitrobenzyl alcohol with glucose (200 mol%) in the presence of NaOH in water-ethanol medium gave 1,2-bis(4-(hydroxymethyl)phenyl)diazene oxide, 1,2-bis(2-(hydroxymethyl)phenyl)diazene oxide and 1,2-bis(4-(1-hydroxyethyl)phenyl)diazene oxide in 76%, 76% and 72% yields, respectively.
  Citation: Molbank
  PubDate: 2022-06-14
  DOI: 10.3390/M1384
  Issue No: Vol. 2022, No. 2 (2022)
Molbank, Vol. 2022, Article M1383:
2-(4-Chlorophenyl)-4-(3,4-dimethoxy-phenyl)-6-methoxy-3-methylquinoline
- Authors: Duván A. Rodríguez Enciso, Carlos E. Puerto Galvis, Vladimir V. Kouznetsov
  Abstract: A 2,4-diarylquinoline derivative, 2-(4-chlorophenyl)-4-(3,4-dimethoxyphenyl)-6-methoxy-3-methylquinoline, was synthesized in a conventional two-step procedure from p-anisidine, p-chlorobenzaldehyde and methyl isoeugenol as available starting reagents through a sequence of BF3·OEt2-catalyzed Povarov cycloaddition reaction/oxidative dehydrogenation aromatization processes under microwave irradiation conditions in the presence of a green oxidative I2-DMSO system. The structure of the compound was fully characterized by FT-IR, 1H and 13C-NMR, ESI-MS, and elemental analysis. Its physicochemical parameters (Lipinski’s descriptors) were also calculated using the Molinspiration Cheminformatics software. The diarylquinoline molecule obtained is an interesting model with increased lipophilicity and thus permeability, an important descriptor for quinoline-based drug design. Such types of derivatives are known for their anticancer, antitubercular, antifungal, and antiviral activities.
  Citation: Molbank
  PubDate: 2022-06-13
  DOI: 10.3390/M1383
  Issue No: Vol. 2022, No. 2 (2022)
Molbank, Vol. 2022, Article M1382: 2,3,5-Tri-O-benzyl-d-xylofuranose
- Authors: Baptiste Taffoureau, Isabelle Gillaizeau, Pascal Retailleau, Cyril Nicolas
  Abstract: The synthesis and crystallization of 2,3,5-tri-O-benzyl-d-xylofuranose permitted us to isolate the alpha anomer with a small contamination of the beta form (ca 10%), whose first crystallographic structure obtained in the P212121 space group was determined at 100 K up to a resolution of sin θmax/λ = 0.71 Å−1 and refined to an R1 value of 0.0171 with a Hirshfeld atom refinement (HAR) approach.
  Citation: Molbank
  PubDate: 2022-06-07
  DOI: 10.3390/M1382
  Issue No: Vol. 2022, No. 2 (2022)
Molbank, Vol. 2022, Article M1381: Bis(μ-iodo)-tetrakis(O-methyl
N-phenylthiocarbamate)-tetraiodo-dibismuth
- Authors: Wafa Arar, Abderrahim Khatyr, Michael Knorr, Carsten Strohmann, Annika Schmidt
  Abstract: In order to investigate the coordination chemistry of O-alkyl N-aryl thiocarbamate ligands, BiI3 was reacted with two equivalents of MeOC(=S)N(H)Ph in MeCN solution to afford the dinuclear title compound complexes [{I2Bi(μ2-I)2BiI2}{κ1-MeOC(=S)N(H)Ph}4] 1. Compound 1 was characterized by IR, UV and NMR spectroscopy, the formation of a dinuclear framework is ascertained by a single-crystal X-ray diffraction study performed at 100 K.
  Citation: Molbank
  PubDate: 2022-06-06
  DOI: 10.3390/M1381
  Issue No: Vol. 2022, No. 2 (2022)
Molbank, Vol. 2022, Article M1380:
- Authors: Aida Šermukšnytė, Ilona Jonuškienė, Kristina Kantminienė, Zigmuntas Jonas Beresnevičius, Ingrida Tumosienė
  Abstract: A synthesis of 2-((4-phenyl-5-(2-(p-tolylamino)ethyl)-4H-1,2,4-triazol-3-yl)thio)-N’-(1-phenylethylidene)acetohydrazide from 2-[(3-{2-[(4-methylphenyl)amino]ethyl}-4-phenyl-4,5-dihydro-1H-1,2,4-triazol-5-yl)sulfanyl]acetohydrazide and acetophenone is reported. The title compound has been tested to possess 1.5-fold higher antioxidant ability than the control, butylated hydroxytoluene, as determined by a Ferric reducing antioxidant power assay.
  Citation: Molbank
  PubDate: 2022-06-05
  DOI: 10.3390/M1380
  Issue No: Vol. 2022, No. 2 (2022)
Molbank, Vol. 2022, Article M1379: Modification of 1-Hexene Vinylidene
Dimer into Primary and Tertiary Alkanethiols
- Authors: Pavel V. Kovyazin, Almira Kh. Bikmeeva, Eldar R. Palatov, Lyudmila V. Parfenova
  Abstract: Aliphatic thiols are in high demand in materials chemistry. Herein, a synthesis of thio-derivatives of 1-hexene vinylidene dimer is described. The approach, based on a hydroalumination reaction with further replacement of the organoaluminum function with sulfur using thiourea or dimethyl disulfide, provides anti-Markovnikov products, 2-butyloctane-1-thiol or 5-(methylsulfanylmethyl)undecane, in moderate yields. The reaction of a vinylidene dimer with phosphorus pentasulfide in the presence of catalytic amounts of (2,2,6,6-tetramethylpiperidin-1-yl)oxyl (TEMPO) selectively gives the Markovnikov product, 5-methylundecane-5-thiol, with a yield of up to 77%.
  Citation: Molbank
  PubDate: 2022-06-04
  DOI: 10.3390/M1379
  Issue No: Vol. 2022, No. 2 (2022)
Molbank, Vol. 2022, Article M1378: Ethyl
(E)-(3-(4-((4-Bromobenzyl)Oxy)Phenyl)Acryloyl)Glycinate
- Authors: Ioannis Fotopoulos, George-Christos Papaioannou, Dimitra Hadjipavlou-Litina
  Abstract: In an attempt to develop new potent anti-inflammatory agents, a cinnamic -amino acid hybrid molecule was synthesized and in silico drug-likeness, in vitro COX-2 inhibition, and pharmacokinetic properties were studied. The results showed high cyclooxygenase inhibitory activity (IC50 = 6 µM) and favorable pharmacokinetic properties, being orally bioavailable according to Lipinski’s rule of five, making this compound a possible lead to design and develop potent COX inhibitors. The new compound, in comparison with its cinnamic acid precursor (E)-(3-(4-((4-bromobenzyl)oxy)phenyl)acrylic acid, showed improved biological activities. Compound ethyl (E)-(3-(4-((4-bromobenzyl)oxy)phenyl)acryloyl)glycinate can be used as a lead for the synthesis of more effective hybrids.
  Citation: Molbank
  PubDate: 2022-06-04
  DOI: 10.3390/M1378
  Issue No: Vol. 2022, No. 2 (2022)
Molbank, Vol. 2022, Article M1377:
6,10-Dichloro-1-oxa-4,8-dithia-7,9-diazaspiro[4.5]deca-6,9-diene
- Authors: Andreas S. Kalogirou, Panayiotis A. Koutentis
  Abstract: Reaction of 3,4,4,5-tetrachloro-4H-1,2,6-thiadiazine with 2-mercaptoethan-1-ol (1 equiv.) gave 6,10-dichloro-1-oxa-4,8-dithia-7,9-diazaspiro[4.5]deca-6,9-diene in 12% yield. The compound was fully characterized.
  Citation: Molbank
  PubDate: 2022-06-03
  DOI: 10.3390/M1377
  Issue No: Vol. 2022, No. 2 (2022)
Molbank, Vol. 2022, Article M1376: Crystal Structure of
N-(2-Benzoyl-4,5-dimethoxyphenethyl)-2-phenylacetamide
- Authors: Petja Marinova, Stoyanka Nikolova, Anna Dołęga, Anife Ahmedova
  Abstract: The crystal structure of N-(2-benzoyl-4,5-dimethoxyphenethyl)-2-phenylacetamide indicates that the compound crystallizes in the monoclinic C2/c space group with eight molecules in the unit cell. The heteroatoms from the amide group form a chain of intermolecular N-H ··· O hydrogen bonds propagating along the b axis. The carbonyl group from the benzoyl substituent participates in short contacts with two H-atoms from the ethyl or phenyl groups.
  Citation: Molbank
  PubDate: 2022-06-01
  DOI: 10.3390/M1376
  Issue No: Vol. 2022, No. 2 (2022)
Molbank, Vol. 2022, Article M1375:
- Authors: Reina Takaki, Bradley O. Ashburn
  Abstract: Imidazole-containing chalcones have been shown to be effective against Aspergillus fumigatus, the pathogenic agent for pulmonary aspergillosis. Claisen-Schmidt condensation of 4-(1H-imidazol-1-yl)benzaldehyde with 3′-chloro-4′-fluoroacetophenone using aqueous sodium hydroxide in methanol yielded the novel compound (E)-3-[4-(1H-imidazol-1-yl)phenyl]-1-(3-chloro-4-fluorophenyl)prop-2-en-1-one in good purity after purification by silica gel column chromatography. This novel compound is suitable for testing the antifungal properties of the combined pharmacophores against Aspergillus and other pathogenic fungi.
  Citation: Molbank
  PubDate: 2022-06-01
  DOI: 10.3390/M1375
  Issue No: Vol. 2022, No. 2 (2022)
Molbank, Vol. 2022, Article M1374: Synthesis and Structure Determination
of
- Authors: Benson M. Kariuki, Bakr F. Abdel-Wahab, Abdelbasset A. Farahat, Gamal A. El-Hiti
  Abstract: A reaction of equimolar equivalents of 1-(4-methoxyphenyl)-5-methyl-1H-1,2,3-triazole-4-carbohydrazide (1) and indoline-2,3-dione (2) in boiling ethanol for 4 h under acidic conditions gave 1-(4-methoxyphenyl)-5-methyl-N’-(2-oxoindolin-3-ylidene)-1H-1,2,3-triazole-4-carbohydrazide (3) in 88% yield. The structure of 3 was ascertained by NMR spectroscopy and single-crystal X-ray diffraction.
  Citation: Molbank
  PubDate: 2022-05-31
  DOI: 10.3390/M1374
  Issue No: Vol. 2022, No. 2 (2022)
Molbank, Vol. 2022, Article M1373: A Convenient Synthesis towards
2-Bromo-2-(methoxy(phenyl)methyl)malononitrile and
2-Iodo-2-(methoxy(phenyl)methyl)malononitrile
- Authors: Jialuo Chen, Lili Duan, Kunming Liu, Jin-Biao Liu
  Abstract: This short note elaborates a concise protocol for the synthesis of two novel vicinal haloethers bearing a malonontrile group, 2-bromo-2-(methoxy(phenyl)methyl)malononitrile (1) and 2-iodo-2-(methoxy(phenyl)methyl)malononitrile (2). The structures of the synthesized compounds were confirmed by 1H, 13C-NMR spectroscopy. The final products indicate that methanol not only acts as solvent but also participates in and dominates the reaction result.
  Citation: Molbank
  PubDate: 2022-05-30
  DOI: 10.3390/M1373
  Issue No: Vol. 2022, No. 2 (2022)
Molbank, Vol. 2022, Article M1372: Synthesis and Structure Determination
of 2-Cyano-3-(1-phenyl-3-(thiophen-2-yl)-1H-pyrazol-4-yl)acrylamide
- Authors: Benson M. Kariuki, Bakr F. Abdel-Wahab, Hanan A. Mohamed, Gamal A. El-Hiti
  Abstract: 2-Cyano-3-(1-phenyl-3-(thiophen-2-yl)-1H-pyrazol-4-yl)acrylamide (3) was synthesized in 90% yield from condensation of equimolar equivalents of 1-phenyl-3-(thiophen-2-yl)-1H-pyrazole-4-carbaldehyde (1) and 2-cyanoacetamide (2) in boiling ethanol under basic condition for 45 min. The structure of 3 was determined using NMR spectroscopy and single crystal X-ray diffraction.
  Citation: Molbank
  PubDate: 2022-05-30
  DOI: 10.3390/M1372
  Issue No: Vol. 2022, No. 2 (2022)
Molbank, Vol. 2022, Article M1371:
5,5’-Thiobis(4-chloro-3H-1,2-dithiole-3-thione)
- Authors: Vladimir A. Ogurtsov, Oleg A. Rakitin
  Abstract: 3H-1,2-Dithiole-3-thiones are important compounds with many types of significant pharmacological activity. Although many derivatives of this class have been described in the literature, their thioethers have not previously been obtained. In this communication, it is shown that the reaction of 4,5-dichloro-3H-1,2-dithiole-3-thione with potassium isocyanate unexpectedly gave 5,5′-thiobis(4-chloro-3H-1,2-dithiole-3-thione). The structure of the synthesized compound was established by elemental analysis, high-resolution mass spectrometry, 13C NMR and IR spectroscopy, and mass spectrometry.
  Citation: Molbank
  PubDate: 2022-05-27
  DOI: 10.3390/M1371
  Issue No: Vol. 2022, No. 2 (2022)
Molbank, Vol. 2022, Article M1370:
- Authors: Ewa Bębenek, Monika Kadela-Tomanek, Elwira Chrobak, Małgorzata Latocha
  Abstract: The reaction of the azidothymidine (AZT) with the 30-propynoylated derivative of 3,28-O,O’-diacetylbetulin gave a 1,4-disubstituted 1,2,3-triazole. The chemical structure of new derivative was characterized by 1H NMR, 13C NMR and HR-MS. The triterpene-AZT conjugate was tested against a human cancer cell lines such as glioblastoma (SNB-19), amelanotic melanoma (C-32), ovarian adenocarcinoma (SKOV-3) and breast cancer (T47D, and MCF-7). 3’-[4-({[3β,28-Bis(acetyloxy)lup-20(29)-en-30-yl]oxy}carbonyl)-1H-1,2,3-triazol-1-yl]-3’-deoxythymidine shown significant activity against MCF-7 cells, with an IC50 value of 4.37 µM.
  Citation: Molbank
  PubDate: 2022-05-26
  DOI: 10.3390/M1370
  Issue No: Vol. 2022, No. 2 (2022)
Molbank, Vol. 2022, Article M1369: Diethyl
2,5-Dihydroxy-3,6-diiodoterephthalate
- Authors: R. Alan Aitken, Niti Schindler, Alexandra M. Z. Slawin
  Abstract: The title compound has been characterised for the first time by the full range of spectroscopic methods, and its X-ray structure shows hydrogen bonded stacks with iodine atoms aligned.
  Citation: Molbank
  PubDate: 2022-05-23
  DOI: 10.3390/M1369
  Issue No: Vol. 2022, No. 2 (2022)
Molbank, Vol. 2022, Article M1368:
- Authors: Timofey N. Chmovzh, Oleg A. Rakitin
  Abstract: (Diphenylamino)phenylethenyl group-containing chromophores are widely employed to design effective materials with useful electronic properties. In this communication, (E)-4-(2-(7-Bromo-[1,2,5]thiadiazolo[3,4-c]pyridin-4-yl)vinyl)-N,N-diphenylaniline was regioselectively obtained by the Heck reaction of 4,7-dibromo-[1,2,5]thiadiazolo[3,4-c]pyridine with N,N-diphenyl-4-vinylaniline. The structure of the newly synthesized compound was established by means of elemental analysis, high resolution mass-spectrometry, 1H, 13C, NOESY NMR, IR and UV spectroscopy and mass-spectrometry.
  Citation: Molbank
  PubDate: 2022-05-19
  DOI: 10.3390/M1368
  Issue No: Vol. 2022, No. 2 (2022)
Molbank, Vol. 2022, Article M1367: Solution Equilibria Formation of
Manganese(II) Complexes with Ethylenediamine, 1,3-Propanediamine and
1,4-ButanediaMine in Methanol
- Authors: José J. N. Segoviano-Garfias, Gabriela A. Zanor, Fidel Ávila-Ramos
  Abstract: Manganese is an abundant element that plays critical roles and is at the reaction center of several enzymes. In order to promote an understanding of the behavior of manganese(II) ion with several aliphatic ligands, in this work, the stability and spectral behavior of the complexes with manganese(II) and ethylenediamine, 1,3-propanediamine or 1,4-butanediamine were explored. A spectrophotometric study of its speciation in methanol was performed at 293 K. The formation constants obtained for these systems were: manganese(II)-ethylenediamine log β110 = 3.98 and log β120 = 7.51; for the manganese(II)-1,3-propanediamine log β110 = 5.08 and log β120 = 8.66; and for manganese(II)-1,4-butanediamine log β110 = 4.36 and log β120 = 8.46. These results were obtained by fitting the experimental spectrophotometric data using the HypSpec software. The complexes reported in this study show a spectral pattern that could be related to a chelate effect in which the molar absorbance is not directly related to the increase in the carbon chain of the ligands.
  Citation: Molbank
  PubDate: 2022-05-18
  DOI: 10.3390/M1367
  Issue No: Vol. 2022, No. 2 (2022)
Molbank, Vol. 2022, Article M1366: Tetraethylammonium
tribromo(triphenylphosphine)nickelate(II)
- Authors: François Baril-Robert, Nicolas Bélanger-Desmarais, Christian Reber
  Abstract: The crystal structure and vibrational spectra of the tetraethylammonium salt of tribromotriphylphosphinonickel(II) is reported. Br-Ni-Br angles vary between 108° and 121°, deviating from perfect tetrahedral angles.
  Citation: Molbank
  PubDate: 2022-05-18
  DOI: 10.3390/M1366
  Issue No: Vol. 2022, No. 2 (2022)
Molbank, Vol. 2022, Article M1365:
2,4-Diamino-5-(nitromethyl)-5H-chromeno[2,3-b]pyridine-3-carbonitrile
- Authors: Yuliya E. Ryzhkova, Fedor V. Ryzhkov, Oleg I. Maslov, Michail N. Elinson
  Abstract: Dimethyl sulfoxide (DMSO) is a cheap polar aprotic solvent used in organic synthesis and in pharmacology because of its low cost, high stability, and non-toxicity. Multicomponent reactions (MCRs) are highly convergent processes and have good atom, step, and pot economies. In this communication, the multicomponent transformation of salicylaldehyde, malononitrile dimer, and nitromethane in DMSO at room temperature was investigated to give 2,4-diamino-5-(nitromethyl)-5H-chromeno[2,3-b]pyridine-3-carbonitrile in good yield. The structure of the earlier unknown compound was confirmed by means of elemental analysis, mass-, nuclear magnetic resonance, and infrared spectroscopy.
  Citation: Molbank
  PubDate: 2022-05-18
  DOI: 10.3390/M1365
  Issue No: Vol. 2022, No. 2 (2022)
Molbank, Vol. 2022, Article M1364: Microwave Assisted Synthesis, Crystal
Structure and Hirshfeld Surface Analysis of Some
2-Formimidate-3-carbonitrile Derivatives Bearing 4H-Pyran and
Dihydropyridine Moieties
- Authors: Sizwe J. Zamisa, Bernard Omondi
  Abstract: Two 4H-pyran- and four dihydropyridine-based 2-formimidate-3-carbonitrile derivatives were synthesized via the conventional solvothermal and microwave radiation methods. The use of the latter technique led to the formation of the desired products in the order of minutes as compared to the former. The formation of the 2-formimidate-3-carbonitrile derivatives was confirmed using spectroscopic techniques whilst the molecular geometry and intermolecular interactions were investigated using single-crystal X-ray diffraction. The formimidate functional group was found to adopt an E configuration in all compounds and this coincides with those of closely related compounds on the Cambridge Structural Database (CSD). Classical but weak intermolecular C—H…O, C—H…N and C—H…π hydrogen bonds were observed in the crystal lattice. According to the Hirshfeld surface analysis, the C—H…π hydrogen bonds contributed the most towards the Hirshfeld surface (14.3–23.9%) than the other two hydrogen bonding types (9.6–12.7%).
  Citation: Molbank
  PubDate: 2022-05-16
  DOI: 10.3390/M1364
  Issue No: Vol. 2022, No. 2 (2022)
Molbank, Vol. 2022, Article M1363: Probing Adamantane Arylhydroxamic Acids
against Trypanosoma brucei and Trypanosoma cruzi
- Authors: Angeliki Sofia Foscolos, Andrew Tsotinis, Martin C. Taylor, John M. Kelly, Ioannis P. Papanastasiou
  Abstract: In this work, we present the synthesis and the anti-trypanosomal activity of the 2-(4-(adamant-1-yl)phenyl)-N-hydroxyarylamides, 1a,b and the 2-(4-(adamant-1-yl)phenoxy)-N-hydroxyacetamide, 1c. The 4-(adamant-1-yl)phenyl- and 4-(adamant-1-yl)phenoxy- moieties, which are endowed with promising drug-like properties, are functionalized at the side chain termini as hydroxamic acids. The phenoxy acetohydroxamic derivative, 1c, shows the most interesting profile in terms of activity and toxicity against trypanosomes and merits further investigation.
  Citation: Molbank
  PubDate: 2022-05-15
  DOI: 10.3390/M1363
  Issue No: Vol. 2022, No. 2 (2022)
Molbank, Vol. 2022, Article M1362:
4-Bromobenzo[1,2-d:4,5-d′]bis([1,2,3]thiadiazole)
- Authors: Timofey N. Chmovzh, Daria A. Alekhina, Timofey A. Kudryashev, Oleg A. Rakitin
  Abstract: Bromoderivatives of benzofused 1,2,5-thiadiazoles are important precursors for the synthesis of dyes, which are widely used to design effective photovoltaic materials. In this study, 4-bromobenzo[1,2-d:4,5-d′]bis([1,2,3]thiadiazole was selectively obtained from the bromination of benzo[1,2-d:4,5-d′]bis([1,2,3]thiadiazole. The structure of the newly synthesized compound was established by means of elemental analysis, high-resolution mass spectrometry, 1H-, 13C-NMR, IR and UV spectroscopy and mass spectrometry.
  Citation: Molbank
  PubDate: 2022-05-12
  DOI: 10.3390/M1362
  Issue No: Vol. 2022, No. 2 (2022)
Molbank, Vol. 2022, Article M1361: Synthesis of 8-Aminoquinoline Amides of
Ursonic and Oleanonic Acid
- Authors: Vladislavs Kroškins, Jevgeņija Lugiņina, Anatoly Mishnev, Māris Turks
  Abstract: 8-Aminoquinoline amides of 3-oxo-olean-12-en-28-oic acid and 3-oxo-urs-12-en-28-oic acid were obtained and characterized by 1H, 13C-NMR and single crystal X-ray analysis. The used triterpenoic acids are oxidized forms of naturally occurring oleanolic acid and ursolic acids. Such types of derivatives are known for their anticancer and antiviral activities. On the other hand, 8-aminoquinoline amides are frequently used for transition metal complexation that is applicable for both C-H activation processes and biological activity studies.
  Citation: Molbank
  PubDate: 2022-05-11
  DOI: 10.3390/M1361
  Issue No: Vol. 2022, No. 2 (2022)
Molbank, Vol. 2022, Article M1360: X-ray Structure Determination of
Naphthalen-2-yl
1-(Benzamido(diethoxyphosphoryl)methyl)-1H-1,2,3-triazole-4-carboxylate
- Authors: Serigne Abdou Khadir Fall, Sara Hajib, Younas Aouine, Rachid Ouarsal, Anouar Alami, Mohamed El Omari, Abderrazzak Assani, Mohamed Saadi, Lahcen El Ammari
  Abstract: We have previously published on a new triazolic phosphonic α-amino ester in position 4 on the triazole ring of a naphthalene ester. The aim of the present paper was to describe its crystallographic study by XRD. The crystal structure of naphthalen-2-yl 1-(benzamido(diethoxyphosphoryl)methyl)-1H-1,2,3-triazole-4-carboxylate was determined by single-crystal X-ray diffraction. This compound crystallizes in the monoclinic system, space group P21/c. The naphthalene system is almost planar and makes dihedral angles of 67.1(2)° and 63.9(2)° with the triazole ring and the phenyl cycle, respectively. The phosphorus atom is surrounded by three oxygen atoms and one carbon atom building a distorted tetrahedron. It is also noted, that one of the two ethyl groups is disordered. In the crystal, the molecules are connected through C-H…O and N-H…O hydrogen bonds to build dimers that are linked together by C-H…O hydrogen bonds, in addition to C-H…π interactions. The presence of an intramolecular hydrogen bond contributes to the stability of the molecular conformation by completing the S(5) cycle.
  Citation: Molbank
  PubDate: 2022-05-10
  DOI: 10.3390/M1360
  Issue No: Vol. 2022, No. 2 (2022)
Molbank, Vol. 2022, Article M1359: Synthesis and Characterization of Two
Isostructural POCOP Ni(II) Pincer Complexes Containing Fluorothiophenolate
Ligands: [Ni(SC6F4-4-H){C6H2-3-(C2H3O)-2,6-(OPiPr2)2}] and
[Ni(SC6F5){C6H2-3-(C2H3O)-2,6-(OPiPr2)2}]
- Authors: Eric G. Morales-Espinosa, Naytze Ortiz-Pastrana, Valente Gómez-Benítez, Reyna Reyes-Martínez, Hilda Amelia Piñón-Castillo, Laura A. Manjarrez-Nevárez, Juan M. German-Acacio, David Morales-Morales
  Abstract: Among their many applications, metal pincer complexes are of interest for their properties as catalysts in cross-coupling reactions. Pincer ligands exhibit tridentate coordination to the metal center and occupy the meridional positions forming two chelate rings. The two Ni(II) POCOP pincer complexes with a fluorothiophenolate ligand reported herein, with formulas [Ni(SC6F4-4-H){C6H2-3-(C2H3O)-2,6-(OPiPr2)2}] (2) and [Ni(SC6F5){C6H2-3-(C2H3O)-2,6-(OPiPr2)2}] (3), are isostructural. Additionally, they are prepared in a facile manner from the chloride compound [NiCl{C6H2-3-(C2H3O)-2-6-(OPiPr2)2}] (1). The complexes exhibited slightly distorted square planar geometries around the metal. The fluorothiophenolate ligands are responsible of the C—H···F, C—F···π and C=O···πF interactions that contribute to stabilize the crystal structure arrays.
  Citation: Molbank
  PubDate: 2022-05-09
  DOI: 10.3390/M1359
  Issue No: Vol. 2022, No. 2 (2022)
Molbank, Vol. 2022, Article M1358: A Concise Synthesis towards
Antimalarial Quinazolinedione TCMDC-125133 and Its Anti-Proliferative
Activity against MCF-7
- Authors: Sitthivut Charoensutthivarakul, Duangporn Lohawittayanan, Phongthon Kanjanasirirat, Kedchin Jearawuttanakul, Sawinee Seemakhan, Suparerk Borwornpinyo, Matthew Phanchana
  Abstract: Quinazolinedione is one of the most notable pharmacophores in drug discovery due to its broad spectrum of biological activities including antimalarial, anticancer, anti-inflammatory, and others. TCMDC-125133, whose structure features a quinazolinedione core, exhibits promising antimalarial activity and low toxicity as described in the GlaxoSmithKline (GSK) report. Herein, a concise four-step synthesis towards quinazolinedione TCMDC-125133 is described using low cost goods and greener alternatives where possible. All synthesized compounds were characterized using polarimetry, IR, NMR, and mass spectrometry. The in-house synthesized TCMDC-125133 was evaluated for its antimalarial activity against P. falciparum 3D7 and antiproliferative activity against MCF-7 cell line.
  Citation: Molbank
  PubDate: 2022-04-21
  DOI: 10.3390/M1358
  Issue No: Vol. 2022, No. 2 (2022)
Molbank, Vol. 2022, Article M1357:
2-(5-Acetyl-7-methoxy-2-(4-methoxyphenyl)benzofuran-3-yl)acetic Acid
- Authors: Boris V. Lichitsky, Andrey N. Komogortsev, Valeriya G. Melekhina
  Abstract: We elaborated a convenient one-step approach for the synthesis of previously unknown 2-(5-acetyl-7-methoxy-2-(4-methoxyphenyl)benzofuran-3-yl)acetic acid. The suggested protocol includes the multicomponent reaction of acetovanillone, 4-methoxyphenylglyoxal and Meldrum’s acid. We have demonstrated that the considered reaction is a one-pot telescoped process including the preliminary condensation of the components in MeCN followed by acid-catalyzed cyclization. The structure of the synthesized product was confirmed by 1H, 13C-NMR spectroscopy and high-resolution mass-spectrometry.
  Citation: Molbank
  PubDate: 2022-04-01
  DOI: 10.3390/M1357
  Issue No: Vol. 2022, No. 2 (2022)
Molbank, Vol. 2022, Article M1356:
- Authors: Jérôme Husson, Laurent Guyard
  Abstract: A new terpyridine molecule, bearing a N-propargylated pyrrole, was prepared and characterized. Its synthesis was based on a Krohnke-type reaction between 2-acetylpyridine and N-propargylpyrrole-2-carboxaldehyde in a basic medium. An allene-containing terpyridine was also obtained as a by-product.
  Citation: Molbank
  PubDate: 2022-03-25
  DOI: 10.3390/M1356
  Issue No: Vol. 2022, No. 2 (2022)
Molbank, Vol. 2022, Article M1355:
6,6′-Di-(2″-thiophenol)-2,2′-bipyridine
- Authors: Yan Huang, Lianpeng Tong
  Abstract: This short note describes the synthesis of compound 6,6′-di-(2″-thiophenol)-2,2′-bipyridine from its methyl phenyl sulfane precursor via deprotection of the methyl groups. The product as well as the intermediate in the synthetic route have been characterized by UV-Vis spectroscopy, 1H- and 13C-NMR spectroscopy, FT-IR spectroscopy, and HR-MS analysis. This work presents a rare example of tetradentate chelators that bears pyridyl backbones and thiophenol donors for the coordination with 3d-transition metal cations.
  Citation: Molbank
  PubDate: 2022-03-24
  DOI: 10.3390/M1355
  Issue No: Vol. 2022, No. 2 (2022)
Molbank, Vol. 2022, Article M1354:
- Authors: Andreas S. Kalogirou, Panayiotis A. Koutentis
  Abstract: Reaction of 4,5-dichloro-1,2,3-dithiazolium chloride with 2-[amino(methylthio)methylene])malononitrile (1 equiv) in the presence of pyridine (2 equiv) gave (Z)-2-{[(4-chloro-5H-1,2,3-dithiazol-5-ylidene)amino](methylthio)methylene}malononitrile in 20% yield. The compound was fully characterized.
  Citation: Molbank
  PubDate: 2022-03-13
  DOI: 10.3390/M1354
  Issue No: Vol. 2022, No. 1 (2022)
Molbank, Vol. 2022, Article M1353: Design, Synthesis and 5-HT1A Binding
Affinity of
N-(3-(4-(2-Methoxyphenyl)piperazin-1-yl)propyl)tricyclo[3.3.1.13,7]decan-1-amine
and
- Authors: Grigoris Zoidis, María Isabel Loza, Marco Catto
  Abstract: Based on previously highlighted structural features, the development of highly selective 5-HT1A receptor inhibitors is closely linked to the incorporation of a 4-alkyl-1-arylpiperazine scaffold on them. In this paper, we present the synthesis of two new compounds bearing the 2-MeO-Ph-piperazine moiety linked via a three carbon atom linker to the amine group of 1-adamantanamine and memantine, respectively. Both were tested for their binding affinity against 5-HT1A receptor. N-(3-(4-(2-methoxyphenyl)piperazin-1-yl)propyl)tricyclo[3.3.1.13,7]decan-1-amine fumarate (8) and N-(3-(4-(2-methoxyphenyl)piperazin-1-yl)propyl)-3,5-dimethyl-tricylo[3.3.1.13,7]decan-1-amine fumarate (10) proved to be highly selective ligands towards 5-HT1A receptor with a binding constant of 1.2 nM and 21.3 nM, respectively, while 5-carboxamidotriptamine (5-CT) (2) was used as an internal standard for this assay with a measured Ki = 0.5 nM.
  Citation: Molbank
  PubDate: 2022-03-10
  DOI: 10.3390/M1353
  Issue No: Vol. 2022, No. 1 (2022)
Molbank, Vol. 2022, Article M1352: In Silico Evaluation of a Promising Key
Intermediate Thieno [2,3-d] Pyrimidine Derivative with Expected JAK2
Kinase Inhibitory Activity
- Authors: Elshaymaa Elmongy, Hanan Henidi
  Abstract: This work describes the synthesis and the cytotoxic evaluation of thiophene and thienopyrimidine derivatives. The investigated compound was subjected to target prediction that indicated its high affinity to kinases and to Janus kinase 2 (JAK2) specifically. Molecular docking screening was performed on three different JAK2 proteins downloaded from the Protein Data Bank (PDB: 5AEP, 4C62 and 3ZMM). In vitro kinase inhibitory activity was evaluated and then compound cytotoxicity was performed on three different cancerous cell lines (HT-29, HepG-2, and MCF-7). Marked cytotoxic activity of the thienopyrimidine derivative against the HepG-2 cell line was demonstrated, reflected by its IC50 value of 8.001 ± 0.0445 μM, which is better than that of the reference standard (IC50 13.91 ± 2.170 μM). Pharmacokinetic studies revealed good well permeability and GI absorption with no violations against Lipinski’s rule.
  Citation: Molbank
  PubDate: 2022-03-09
  DOI: 10.3390/M1352
  Issue No: Vol. 2022, No. 1 (2022)
Molbank, Vol. 2022, Article M1351:
- Authors: Xiaoyun Yun, Yuhan Xie, Jerome P. L. Ng, Betty Yuen Kwan Law, Vincent Kam Wai Wong, Paolo Coghi
  Abstract: The 1,2,3-triazole ring system can be easily obtained by copper-catalyzed click reaction of azides with alkynes. 1,2,3-Triazole exhibits a myriad of biological activities, including antimalarial, antibacterial, and antiviral activities. We herein reported the synthesis of quinoline-based [1,2,3]-triazole hybrid via Cu(I)-catalyzed click reaction of 4-azido-7-chloroquinoline with alkyne derivative of 2-bromobenzaldehyde. The compound was fully characterized by proton nuclear magnetic resonance (1H-NMR), carbon-13 nuclear magnetic resonance (13C-NMR), heteronuclear single quantum coherence (HSQC), ultraviolet (UV), and high-resolution mass spectroscopies (HRMS). This compound was screened in vitro against two different normal cell lines. Preliminary studies attempted to evaluate its interaction with Delta RBD of spike protein of SARS-CoV-2 by bio-layer interferometry. Finally, the drug-likeness of the compound was also investigated by predicting its pharmacokinetic properties.
  Citation: Molbank
  PubDate: 2022-03-09
  DOI: 10.3390/M1351
  Issue No: Vol. 2022, No. 1 (2022)
Molbank, Vol. 2022, Article M1350: Synthesis of New
1,2,3,4-Tetrahydroquinoline Hybrid of Ibuprofen and Its Biological
Evaluation
- Authors: Stanimir Manolov, Iliyan Ivanov, Dimitar Bojilov
  Abstract: Herein we report the obtaining of 1-(3,4-dihydroquinolin-1(2H)-yl)-2- (4-isobutylphenyl)propan-1-one and its characterization. The newly obtained hybrid and its derivatives (hybrids of ibuprofen with 1,2,3,4-tetrahydroisoquinoline, and piperidine) were screened for their in vitro antioxidant, antitryptic, and inhibition of albumin denaturation activity. The lipophilicity was established using both reversed-phase thin layer chromatography and in silico calculations.
  Citation: Molbank
  PubDate: 2022-03-07
  DOI: 10.3390/M1350
  Issue No: Vol. 2022, No. 1 (2022)
Molbank, Vol. 2022, Article M1349:
- Authors: Vincenzo Piccialli
  Abstract: In this note we report the synthesis of a doubly acylated cis-THF-diol product synthesised in three steps by the stereoselective RuO4-catalysed oxidative cyclisation of 1,5-hexadiene, followed by benzoylation and acetylation. This substance is one of the substrates chosen to probe a new developed oxidative procedure to transform bis-acylated THF-diols into bis-acylated 1,4-diketones. This new derivative was fully characterised by spectroscopic methods.
  Citation: Molbank
  PubDate: 2022-03-04
  DOI: 10.3390/M1349
  Issue No: Vol. 2022, No. 1 (2022)
Molbank, Vol. 2022, Article M1348:
6-(2′-(4″-Oxabutyloxy)phenyl)-1,6,11-triaza-3,9,14,17,22,25-hexaoxa-2(1,2)(4-methylbenzena)-10(1,2)(5-methylbenzena)bicyclo(9.8.8)heptacosaphane
Sodium Bromide Dichloromethane
- Authors: Matthias Jochem, Dieter Schollmeyer, Heiner Detert
  Abstract: Potassium ion sensors are important for the study of concentration profiles in tissues. The synthesis of a cryptand suited for potassium ions and the crystal structure of it with a chelated sodium ion are presented.
  Citation: Molbank
  PubDate: 2022-03-03
  DOI: 10.3390/M1348
  Issue No: Vol. 2022, No. 1 (2022)
Molbank, Vol. 2022, Article M1347: Synthesis and Crystal Structure of
9,12-Dibromo-ortho-Carborane
- Authors: Olga B. Zhidkova, Anna A. Druzina, Sergey A. Anufriev, Kyrill Yu. Suponitsky, Igor B. Sivaev, Vladimir I. Bregadze
  Abstract: Synthesis, NMR spectral data and crystal structure of 9,12-dibromo derivative of ortho-carborane are reported.
  Citation: Molbank
  PubDate: 2022-03-01
  DOI: 10.3390/M1347
  Issue No: Vol. 2022, No. 1 (2022)
Molbank, Vol. 2022, Article M1346:
O-((Ferrocenyl)(3-fluorophenyl)methyl)hydroxylamine
- Authors: Angeliki S. Foscolos, Maria Georgiou, Minas S. Papadopoulos, Aristeidis Chiotellis
  Abstract: Based on the diaryl hydroxylamine scaffold, which exhibits the potential to inhibit all three enzymes of the first step of the kynurenine pathway, the main tryptophan degradation pathway in mammals, which is often activated in cancer, we report herein the synthesis of a ferrocenyl analogue as an attempt to improve the scaffold’s pan-inhibitory potency through the isosteric replacement of a phenyl group with the ferrocenyl moiety. The synthetic methodology followed gives access to O-((ferrocenyl)(aryl)methyl)hydroxylamines, a class of compounds not yet reported in the literature.
  Citation: Molbank
  PubDate: 2022-03-01
  DOI: 10.3390/M1346
  Issue No: Vol. 2022, No. 1 (2022)
Molbank, Vol. 2022, Article M1345:
- Authors: Maria Marzano, Monica Terracciano, Vincenzo Piccialli, Ahmed Mahal, Roberto Nilo, Stefano D’Errico
  Abstract: Cyclic adenosine diphosphate ribose (cADPR) is a cyclic nucleotide involved in the Ca2+ homeostasis. In its structure, the northern ribose, bonded to adenosine through an N1 glycosidic bond, is connected to the southern ribose through a pyrophosphate bridge. Due to the chemical instability at the N1 glycosidic bond, new bioactive cADPR derivatives have been synthesized. One of the most interesting analogues is the cyclic inosine diphosphate ribose (cIDPR), in which the hypoxanthine replaced adenosine. The efforts for synthesizing new linear and cyclic northern ribose modified cIDPR analogues led us to study in detail the inosine N1 alkylation reaction. In the last few years, we have produced new flexible cIDPR analogues, where the northern ribose has been replaced by alkyl chains. With the aim to obtain the closest flexible cIDPR analogue, we have attached to the inosine N1 position a 2″,3″-dihydroxypentyl chain, possessing the two OH groups in a ribose-like fashion. The inosine alkylation reaction afforded also the O6-alkylated regioisomer, which could be a useful intermediate for the construction of new kinds of cADPR mimics.
  Citation: Molbank
  PubDate: 2022-03-01
  DOI: 10.3390/M1345
  Issue No: Vol. 2022, No. 1 (2022)
Molbank, Vol. 2022, Article M1344: Charge-Transfer Adducts of
Chalcogenourea Derivatives of N-Heterocyclic Carbenes with Iodine
Monochloride
- Authors: Marina Saab, Fady Nahra, Kristof Van Hecke
  Abstract: In this communication, we investigate the reaction between seleno- and thiourea, derived from N-heterocyclic carbenes, with the interhalogen iodine monochloride. The formation of all three products was confirmed by NMR spectroscopy, while single-crystal X-ray analyses were able to establish a charge-transfer coordination type, which showed a linear Se/S-I-Cl arrangement, for all adducts formed. Based on a detailed crystallographic analysis, we can deduce the zwitterionic character of these compounds.
  Citation: Molbank
  PubDate: 2022-02-23
  DOI: 10.3390/M1344
  Issue No: Vol. 2022, No. 1 (2022)
Molbank, Vol. 2022, Article M1343: Synthesis of Novel
Pyrazolo[3,4-b]pyridines with Affinity for β-Amyloid Plaques
- Authors: Veroniki P. Vidali, Georgia Nigianni, Georgia D. Athanassopoulou, Aleksander Canko, Barbara Mavroidi, Dimitris Matiadis, Maria Pelecanou, Marina Sagnou
  Abstract: Three novel pyrazolo[3,4-b]pyridines were synthesized via the cyclization of 5-amino-1-phenylpyrazole with the corresponding unsaturated ketone in the catalytic presence of ZrCl4. The ketones were afforded by modifying a stabilized ylide facilitated Wittig reaction in fairly high yields. The novel compounds exhibited exciting photophysical properties with the dimethylamine phenyl-bearing pyrazolopyridine showing exceptionally large Stoke’s shifts. Finally, both the dimethylamino- and the pyrene-substituted compounds demonstrated high and selective binding to amyloid plaques of Alzheimer’s disease (AD) patient brain slices upon fluorescent confocal microscopy observation. These results reveal the potential application of pyrazolo[3,4-b]pyridines in the development of AD amyloid plaque probes of various modalities for AD diagnosis.
  Citation: Molbank
  PubDate: 2022-02-22
  DOI: 10.3390/M1343
  Issue No: Vol. 2022, No. 1 (2022)
Molbank, Vol. 2022, Article M1342: A Simple and Efficient Approach to the
Synthesis of 4-Aryl-2-dialkylphosphonomethyl-4-oxobutanenitrile
- Authors: Ferid Yaccoubi, Hitham Elleuch, Hussein S. Mohamed, Zeinab S. Hamza, Yasser H. Zaki
  Abstract: In this work, we describe a simple and easy synthetic approach to variously 4-aryl-2-alkylphosphonomethyl-4-oxobutanenitrile based on the reaction of aromatic aldehydes with phosphorylated Michael’s acceptors in good yields. A general mechanism for the reactions was also proposed. Characterization of the products was carried out by several spectroscopic tools, including Infrared and Nuclear Magnetic Resonance Spectroscopies (1H, 13C, and 31P-NMR). Molecular docking studies were conducted on the synthesized materials against (1UK4) the crystal structure of the SARS Coronavirus Main Proteinase (3CLpro) to study the antiviral activity of these compounds and against (1E3K) the Human Progesterone Receptor to study the anticancer activity of these compounds. We found that compound (5i) was the best one in both antiviral and anticancer activity (according to the binding energy values).
  Citation: Molbank
  PubDate: 2022-02-15
  DOI: 10.3390/M1342
  Issue No: Vol. 2022, No. 1 (2022)
Molbank, Vol. 2022, Article M1341: Synthesis of
3-Aroyl-4-heteroarylpyrrole Derivatives by the Van Leusen Method
- Authors: Jorge Trilleras, Jairo Quiroga, Angelina Hormaza
  Abstract: The synthesis and structural diversification of N-heterocycles systems have attracted much attention because of their potential applications. Three 6-aryl-3-methyl-1-phenyl-1H-pyrazolo[3,4-b]pyridine-5-carbaldehyde 4 derivatives, in reaction with acetophenones 5, via conventional Claisen–Schmidt condensation reactions, generated the respective enones. The enones were used as electron-deficient olefins in a “formal” [2+3] cycloaddition reaction using p-tosylmethyl isocyanide—TosMIC 7. This protocol allows access to 3-(substituted aroyl)-4-heteroaryl pyrrole derivatives by the Van Leusen method.
  Citation: Molbank
  PubDate: 2022-02-15
  DOI: 10.3390/M1341
  Issue No: Vol. 2022, No. 1 (2022)
Molbank, Vol. 2022, Article M1340: Ethyl
5-Formyl-1-(pyridin-3-yl)-1H-1,2,3-triazole-4-carboxylate: Synthesis,
Crystal Structure, Hirshfeld Surface Analysis, and DFT Calculation
- Authors: Nazariy T. Pokhodylo, Yuriy I. Slyvka, Evgeny A. Goreshnik, Mykola D. Obushak
  Abstract: For the first time, 5-formyl-1-(pyridin-3-yl)-1H-1,2,3-triazole-4-carboxylate was synthesized via a two-step scheme. The molecular structure of the compound was determined by a single-crystal X-ray diffraction analysis. The Hirshfeld surface analysis was used to study various intermolecular interactions. The crystalline structure is marked by the presence of three types of π-interactions (n→π*, lp···π, and π···π) between the -C(H)=O group and triazole rings. The compound is a versatile polyfunctional building block for construction of annulated 1,2,3-triazoles.
  Citation: Molbank
  PubDate: 2022-02-15
  DOI: 10.3390/M1340
  Issue No: Vol. 2022, No. 1 (2022)
Molbank, Vol. 2022, Article M1339:
6-Chloro-3H-benzo[d][1,2,3]dithiazol-2-ium Chloride
- Authors: Alexander J. Nicholls, Ian R. Baxendale
  Abstract: This short note describes the synthesis of an amorphous benzo[1,2,3]dithiazole chloride salt (commonly known as a ‘Herz salt’) by use of the Herz reaction. Hetero- and homolytic transformations of this species to a variety of useful adducts in medicinal and materials chemistry are well established, although there are limited examples of isolation in the literature, and characterisation data is even harder find. While several studies have confirmed the structure of the benzodithiazole ring beyond doubt, (having generated suitably crystalline salts with large counterions for XRD-analysis), there remains value in understanding and optimising the synthesis of the simple, amorphous polymorphs. For the first time, MS data is provided for this compound and a new mechanism of its formation is proposed based upon new experimental observations and data.
  Citation: Molbank
  PubDate: 2022-02-11
  DOI: 10.3390/M1339
  Issue No: Vol. 2022, No. 1 (2022)
Molbank, Vol. 2022, Article M1338: Ethyl
- Authors: Susana M. M. Lopes, Américo Lemos, José A. Paixão, Teresa M. V. D. Pinho e Melo
  Abstract: The Diels–Alder reaction of ethyl 3-(1-phenyl-1H-tetrazol-5-yl-1,2-diaza-1,3-butadiene-1-carboxylate with 2-acetyl-6-methyl-2,3-dihydro-4H-pyran (methyl vinyl ketone dimer) regioselectively afforded the corresponding 3-(tetrazol-5-yl)-hexahydro-7H-pyrano[2,3-c]pyridazine in quantitative yield. An X-ray crystal structure of this cycloadduct is reported.
  Citation: Molbank
  PubDate: 2022-02-10
  DOI: 10.3390/M1338
  Issue No: Vol. 2022, No. 1 (2022)
Molbank, Vol. 2022, Article M1337:
(1R,2R,3S,4R)-1-(Acetylamino)-2,4,5-tris(acetyloxy)-1-((2S)-4-(benzyloxy)-5-oxo-2,5-dihydrofuran-2-yl)pentan-3-yl
Acetate
- Authors: Liam S. Fitzgerald, Ciaran O’Malley, Paul V. Murphy
  Abstract: Treatment of N-acetylneuraminic acid with excess base in the presence of benzyl bromide gives a polyhydroxylated 1,4 lactone which after acetylation gave the title compound in 20% overall yield. The structure of the product was confirmed by single crystal X-ray diffraction analysis, as well as FT-IR, NMR spectroscopic and HRMS analysis.
  Citation: Molbank
  PubDate: 2022-02-10
  DOI: 10.3390/M1337
  Issue No: Vol. 2022, No. 1 (2022)
Molbank, Vol. 2022, Article M1336: Barium
5-(tert-butyl)-2,3-dihydroxybenzenesulfonate
- Authors: Lyubov G. Rubicheva, Daniil A. Lukyanov
  Abstract: Catechols and their derivatives attract great scientific interest due to the broad spectrum of their functional properties, including complexation, redox behavior, association ability and antioxidant activity. Because of the low molecular mass and two-electron redox process, they are considered to be a promising energy storage compound in different types of electrochemical power sources, such as metal-ion batteries or redox flow batteries. Herein, we report a preparation of the sterically hindered sulfonated catechol, namely the barium salt of 5-(tert-butyl)-2,3-dihydroxybenzenesulfonic acid, by the direct sulfonation of 4-tert-butylcatechol, by concentrated sulfuric acid. The proposed procedure is green and atom-economic, providing the desired product in high yield after simple purification. The solvent-free procedure is inexpensive and highly scalable, which enables direct industrial production of the title product. The resulting product was characterized by the 1H and 13C nuclear magnetic resonance (NMR) and ESI-high resolution mass spectrometry (ESI-HRMS).
  Citation: Molbank
  PubDate: 2022-02-09
  DOI: 10.3390/M1336
  Issue No: Vol. 2022, No. 1 (2022)
Molbank, Vol. 2022, Article M1335: Crystal Structure of a Chiral
Sec-Amine, 4-Chloro-N-(1-(pyridin-2-yl)ethyl)aniline
- Authors: Adesola A. Adeleke, Bernard Omondi
  Abstract: In this communication, we present the crystal structure of a secondary amine: 4-chloro-N-(1-(pyridin-2-yl)ethyl)aniline (Lb) obtained from a stepwise reduction of an imine, (E)-N-(4-chlorophenyl)-1-(pyridin-2-yl)ethan-1-imine (La) with sodium borohydride. The structure was characterized by FT-IR, 1H and 13C NMR, Mass Spectroscopy and X-ray diffraction.
  Citation: Molbank
  PubDate: 2022-02-09
  DOI: 10.3390/M1335
  Issue No: Vol. 2022, No. 1 (2022)
Molbank, Vol. 2022, Article M1334:
- Authors: Steven G. Dannenberg, Rory Waterman
  Abstract: Copper phosphido compound Cu4(μ-PPh2)4(PtBu3)2 was synthesized by three synthetic methods and structurally characterized by X-ray diffraction and 1H, 31P, 13C and 31P HMBC NMR spectroscopy. Cu4(μ-PPh2)4(PtBu3)2 was also demonstrated to be a hydrophosphination pre-catalyst.
  Citation: Molbank
  PubDate: 2022-02-09
  DOI: 10.3390/M1334
  Issue No: Vol. 2022, No. 1 (2022)
Molbank, Vol. 2022, Article M1333: Synthesis, Crystal Structure and
Anti-Leukemic Activity of
- Authors: Jean Guillon, Solène Savrimoutou, Sandra Albenque-Rubio, Noël Pinaud, Stéphane Moreau, Vanessa Desplat
  Abstract: 1,3-Dihydro-1-{1-[4-(4-phenylpyrrolo[1,2-a]quinoxalin-3-yl)benzyl]piperidin-4-yl}-2H-benzimidazol-2-one has been synthesized through a multi-step pathway starting from commercially available 2-nitroaniline. A structure characterization of this new substituted pyrrolo[1,2-a]quinoxaline compound was achieved by using FT-IR, 1H-NMR, 13C-NMR, X-Ray and HRMS spectral analysis. This new pyrroloquinoxaline derivative shows an interesting cytotoxic potential against several human leukemia cell lines (HL60, K562 and U937 cells).
  Citation: Molbank
  PubDate: 2022-02-09
  DOI: 10.3390/M1333
  Issue No: Vol. 2022, No. 1 (2022)
Molbank, Vol. 2022, Article M1332:
- Authors: Timofey Chmovzh, Vladislav Korshunov, Ilya Taydakov, Oleg Rakitin
  Abstract: Donor molecules of the D-π-A-π-D type structure are often used for applications in organic photovoltaics. In this communication, bromination of 4,7-di(thiophen-2-yl)-[1,2,5]thiadiazolo[3,4-d]pyridazine followed by Suzuki cross-coupling with carbazoleboronic acid gave 4,7-bis( 5-(9-hexyl-9H-carbazol-3-yl)thiophen-2-yl)-[1,2,5]thiadiazolo[3,4-d]pyridazine. The structure of the newly synthesized compounds was established by high resolution mass-spectrometry, 1H, 13C NMR, IR, and UV spectroscopy and mass-spectrometry. A study of the luminescent properties of the dye showed that it exhibits fluorescence in the near infrared region of the spectrum, which makes it a promising compound for use as an active emitting layer in NIR OLED as well as for other possible applications as an IR luminophore.
  Citation: Molbank
  PubDate: 2022-02-08
  DOI: 10.3390/M1332
  Issue No: Vol. 2022, No. 1 (2022)
Molbank, Vol. 2022, Article M1331: Synthesis and Antimicrobial Evaluation
of
2-(6-Imidazo[1,2-a]pyridin-2-yl-5-methyl-2,4-dioxo-3-phenyl-3,4-dihydrothieno[2,3-d]pyrimidin-1(2H)-yl)-N-arylacetamide
Derivatives
- Authors: Sergiy V. Vlasov, Hanna I. Severina, Oleksandr V. Borysov, Konstantin Yu. Krolenko, Pavlo E. Shynkarenko, Narzullo B. Saidov, Vitaliy S. Vlasov, Victoriya A. Georgiyants
  Abstract: 6-Heteryl-5-methylthieno[2,3-d]pyrimidin-2,4(1H,3H)-diones are of great interest as the promising objects for the search of antibacterials. In this communication, we obtained 6-(imidazo[1,2-a]pyridin-2-yl)-5-methyl-3-phenylthieno[2,3-d]pyrimidine-2,4(1H,3H)-dione by interaction of 6-(bromoacetyl)-5-methyl-3-phenylthieno[2,3-d]pyrimidine-2,4(1H,3H)-dione with 2-aminopyridine. The obtained heterocyclic hybrid was further modified by alkylation with 2-chloroarylacetamides. Antimicrobial activity studies for the synthesized compounds using the agar well diffusion method revealed their moderate activity against S. aureus, E. coli and B. subtilis. According to the double dilution assay MIC value results for 6-(imidazo[1,2-a]pyridin-2-yl)-5-methyl-3-phenylthieno[2,3-d]pyrimidine-2,4(1H,3H)-dioneagainst P. aeruginosa was less than the value determined for the reference drug streptomycin. The docking study of the synthesized compounds to the active site of TrmD isolated from P. aeruginosa did not show their effective inhibitory activity.
  Citation: Molbank
  PubDate: 2022-02-07
  DOI: 10.3390/M1331
  Issue No: Vol. 2022, No. 1 (2022)
Molbank, Vol. 2022, Article M1330:
- Authors: José Edmilson Ribeiro do Nascimento, Daniela Hartwig, Raquel Guimarães Jacob, Márcio Santos Silva
  Abstract: Here we describe the functionalization of lupulone natural compound in obtaining 3-isobutyl-5,5,7-tris(3-methylbut-2-en-1-yl)-1-phenyl-1,7-dihydro-4H-indazole-4,6(5H)-dione. The lupulone-H-indazole derivative was prepared with 75% yield through the reaction between lupulone and phenyl-hydrazine employing SiO2/ZnCl2 (30% m/m) as a support solid in a solvent-free condition. Based on the possibilities of products, a complete NMR structural characterization of this lupulone-H-indazole was performed by 1H, 13C{1H}, COSY, HSQC and HMBC NMR experiments, showing an important contribution in producing the first results related to lupulone reactivity.
  Citation: Molbank
  PubDate: 2022-02-01
  DOI: 10.3390/M1330
  Issue No: Vol. 2022, No. 1 (2022)
Molbank, Vol. 2022, Article M1329: Quercetin Hybrids—Synthesis,
Spectral Characterization and Radical Scavenging Potential
- Authors: Desislava Kirkova, Yordan Stremski, Stela Statkova-Abeghe, Margarita Docheva
  Abstract: New quercetin-based derivatives are synthesized in an easily accessible one-pot manner. The method is based on the reaction of quercetin with in situ formed electrophilic N-alkoxycarbonylazolium ions. The position of the newly formed C-C bond and structure were spectrally characterized by 1D, 2D 1H, 13C-NMR, IR, and MS analysis. Thus, in all cases, good regioselectivity in the C-8 position for the obtained products was demonstrated. The obtained compounds were evaluated for their DPPH and ABTS free radical scavenging activity and compared to natural compounds—quercetin and rutin.
  Citation: Molbank
  PubDate: 2022-01-30
  DOI: 10.3390/M1329
  Issue No: Vol. 2022, No. 1 (2022)
Molbank, Vol. 2022, Article M1328:
- Authors: Ihor Yushyn, Serhii Holota, Roman Lesyk
  Abstract: The pharmacophore hybridization approach is widely used for the design of drug-like small molecules with anticancer properties. In the present work, a “cost-effective” approach to the synthesis of the novel non-condensed pyrazoline-bearing hybrid molecule with 1,3,4-thiadiazole and dichloroacetic acid moieties is proposed. The 5-amino-1,3,4-thiadiazole-2-thiol was used as a starting reagent, and the synthetic strategy includes stepwise alkylation of the sulfur atom and acylation of the nitrogen atom to obtain the target title compound. The structure of the synthesized 2,2-dichloro-N-[5-[2-[3-(4-methoxyphenyl)-5-phenyl-3,4-dihydro-2H-pyrazol-2-yl]-2-oxoethyl]sulfanyl-1,3,4-thiadiazol-2-yl]acetamide (yield 90%) was confirmed by 1H, 13C, 2D NMR and LC-MS spectra. Anticancer activity in “60 lines screening” (NCI DTP protocol) was studied in vitro for the title compound.
  Citation: Molbank
  PubDate: 2022-01-28
  DOI: 10.3390/M1328
  Issue No: Vol. 2022, No. 1 (2022)
Molbank, Vol. 2022, Article M1327: N,N′-Diarylformamidine
Dithiocarbamate Ag(I) Cluster and Coordination Polymer
- Authors: Segun D. Oladipo, Bernard Omondi
  Abstract: An Ag(I)formamidine cluster Ag6L16 (1) and an Ag(I)formamidine coordination polymer Ag7(L2)2 2 (L1 = N,N′-bis(2,6-disopropylphenyl) formamidine dithiocarbamate and L2 = N,N′-mesityl formamidine dithiocarbamate) have been synthesized from the reactions of L1 and L2 with AgNO3 respectively. The complexes were characterized using spectroscopic and analytical methods, including single-crystal X-ray diffraction. In the structure of 1, a six vertex distorted square bi-pyramidal octahedron is formed from an Ag6 core. The N,N′-bis(2,6-disopropylphenyl) formamidine dithiocarbamate ligands stabilize this core through two main –CS2 bridging modes giving a propeller like structure. In the structure of 2, each of the two Ag(I) centers are bridged by two N,N′-mesityl formamidine dithiocarbamate ligands forming 8-member Ag2(CS2)2 metallacycles with an inversion center in the middle of the Ag—Ag argentophilic bond. The metallacycles are connected through Ag—S bonds forming ribbons in the crystallographic a-axis. The Ag(I) centers are coordinated to two N,N′-mesitylformamidine dithiocarbamates through the dithiocarbamate S atoms. The thermal decomposition of complexes 1 and 2 had similar thermograms with one major weight loss activity and the formation of elemental silver particles thereafter.
  Citation: Molbank
  PubDate: 2022-01-28
  DOI: 10.3390/M1327
  Issue No: Vol. 2022, No. 1 (2022)
Molbank, Vol. 2022, Article M1325: Acknowledgment to Reviewers of Molbank
in 2021
- Authors: Molbank Editorial Office Molbank Editorial Office
  Abstract: Rigorous peer-reviews are the basis of high-quality academic publishing [...]
  Citation: Molbank
  PubDate: 2022-01-27
  DOI: 10.3390/M1325
  Issue No: Vol. 2022, No. 1 (2022)
Molbank, Vol. 2022, Article M1326: 2-Nitro-1-vinyl-1H-imidazole
- Authors: Afonso Santine M. M. Velez, Gabriela Alves de Souza, Paulo Pitasse-Santos, Douglas Chaves de Alcântara Pinto, Debora Decote-Ricardo, Marco Edilson Freire de Lima
  Abstract: Nitroimidazoles are pharmacophoric groups responsible for important antiparasitic activity against several infectious diseases. 2-Nitroimidazoles are found in some antiparasitic drugs and are one of the main moieties responsible for the biological activities exhibited. As an example, we can mention the drug benznidazole, the only drug available in Brazil for the treatment of Chagas disease. This work describes an efficient methodology for the synthesis of 2-nitro-1-vinyl-1H-imidazole through a simple and direct approach, as well as its full characterization and biological assessment. The antiparasitic evaluation of 2-nitro-1-vinyl-1H-imidazole against Trypanosoma cruzi (Tulahuen C2C4-LacZ strain) showed IC50 = 4.8 μM on amastigotes and low cytotoxicity against LLC-MK2 cells (IC50 > 500 μM), validating 2-nitro-1-vinyl-1H-imidazole as a biologically active structural subunit for anti-T. cruzi activity. The results presented herein demonstrate that 2-nitro-1-vinyl-1H-imidazole can be easily obtained, possessing great potential for use in the design of new antichagasic drugs through a molecular hybridization strategy using known coupling reactions.
  Citation: Molbank
  PubDate: 2022-01-27
  DOI: 10.3390/M1326
  Issue No: Vol. 2022, No. 1 (2022)
Molbank, Vol. 2022, Article M1324: 3-Carbamoylmethyl-Indole-1-Carboxylic
Acid Ethyl Ester
- Authors: Yordanka Mollova, Plamen Angelov, Pavel Yanev
  Abstract: 3-Carbamoylmethyl-Indole-1-Carboxylic Acid Ethyl Ester (an ethoxycarbonyl derivative of indole-3-acetamide) is obtained by Friedel–Crafts type cyclocondensation of γ-functionalized acetoacetamide in neat polyphosphoric acid.
  Citation: Molbank
  PubDate: 2022-01-26
  DOI: 10.3390/M1324
  Issue No: Vol. 2022, No. 1 (2022)
Molbank, Vol. 2022, Article M1323:
- Authors: Evita Romanovska, Aleksandrs Pučkins, Tatjana Grigorjeva, Elena Kirilova
  Abstract: We report a synthesis of 3-bromo-9-N′-(N,N-dimethylformamidino)benzanthrone in good yield by a condensation reaction of 3-bromo-9-aminobenzanthrone with dimethylformamide in the presence of phosphorous oxychloride. The structure of the synthesized amidine was characterized by FTIR-ATR, NMR experiments, and elemental analysis. The title compound was analyzed by UV-Vis and fluorescence spectroscopy in various organic solvents.
  Citation: Molbank
  PubDate: 2022-01-25
  DOI: 10.3390/M1323
  Issue No: Vol. 2022, No. 1 (2022)
Molbank, Vol. 2022, Article M1322: Reaction of
4,5-Dichloro-1,2,3-dithiazolium Chloride with
2-(Phenylsulfonyl)acetonitrile
- Authors: Konstantinos Plakas, Andreas S. Kalogirou, Andreas Kourtellaris, Panayiotis A. Koutentis
  Abstract: The reaction of 4,5-dichloro-1,2,3-dithiazolium chloride with 2-(phenylsulfonyl)acetonitrile (1 equiv) in the presence of pyridine (2 equiv) gave S-(3-chloro-5-cyanoisothiazol-4-yl)benzenesulfonothioate and (Z)-2-(4-chloro-5H-1,2,3-dithiazol-5-ylidene)-2-(phenylsulfonyl)acetonitrile in 19% and 23% yield, respectively. The compounds were fully characterized and the mechanistic rationale is proposed for the formation of the benzensulfonate.
  Citation: Molbank
  PubDate: 2022-01-24
  DOI: 10.3390/M1322
  Issue No: Vol. 2022, No. 1 (2022)
Molbank, Vol. 2022, Article M1321: Reactions of 4H-1,2,6-Thiadiazine
Sulfides
- Authors: Andreas S. Kalogirou, Panayiotis A. Koutentis
  Abstract: 3,5-Dichloro-4H-1,2,6-thiadiazin-4-one reacts with benzo[d]thiazole-2-thiol (1 equiv) and triethylamine (1 equiv) to give 3-(benzo[d]thiazol-2-ylthio)-5-chloro-4H-1,2,6-thiadiazin-4-one in 71% yield. The reactivity of this compound with methoxide is explored and compared with that of 3-chloro-5-(phenylthio)-4H-1,2,6-thiadiazin-4-one.
  Citation: Molbank
  PubDate: 2022-01-21
  DOI: 10.3390/M1321
  Issue No: Vol. 2022, No. 1 (2022)
Molbank, Vol. 2022, Article M1320:
- Authors: R. Alan Aitken, Fiona M. Fotherby, Alexandra M. Z. Slawin
  Abstract: The title epoxide was obtained by spontaneous epoxidation of the corresponding unsaturated imide in air or by peracid oxidation. Unambiguous assignment of the 1H- and 13C-NMR spectra is achieved by comparison between analogous compounds and its X-ray structure confirms the exo,exo-configuration.
  Citation: Molbank
  PubDate: 2022-01-20
  DOI: 10.3390/M1320
  Issue No: Vol. 2022, No. 1 (2022)
Molbank, Vol. 2022, Article M1319:
- Authors: Stanimir Manolov, Iliyan Ivanov, Dimitar Bojilov
  Abstract: 2-(2-fluoro-[1,1′-biphenyl]-4-yl)-N-(1-phenylpropan-2-yl)propanamide was synthesized by a reaction between amphetamine and flurbiprofen in high yields. The newly obtained hybrid molecule was fully analyzed and characterized via 1H, 13C, UV, IR, HPLC, and mass spectral data.
  Citation: Molbank
  PubDate: 2022-01-17
  DOI: 10.3390/M1319
  Issue No: Vol. 2022, No. 1 (2022)
Molbank, Vol. 2022, Article M1318:
2,2′-(Ethane-1,2-diyl)bis(4-chlorophenol)
- Authors: R. Alan Aitken, Anna L. G. Gidlow, Russel S. Ramsewak, Alexandra M. Z. Slawin
  Abstract: The X-ray structure of the title compound, obtained as a byproduct in a natural product synthesis, has been determined and shows an unusual pattern featuring chains of molecules with both intra- and intermolecular hydrogen bonding of the OH groups.
  Citation: Molbank
  PubDate: 2022-01-14
  DOI: 10.3390/M1318
  Issue No: Vol. 2022, No. 1 (2022)
Molbank, Vol. 2022, Article M1317:
- Authors: Yuliya E. Ryzhkova, Varvara M. Kalashnikova, Fedor V. Ryzhkov, Michail N. Elinson
  Abstract: Michael addition–halogenation–intramolecular ring-closing (MHIRC) reactions are processes in which a halogen atom as a leaving group can attach to substrates or reactants during the reaction, which then undergoes intramolecular ring closure. In this communication the MHIRC transformation of 4-benzylidene-3-phenylisoxazol-5(4H)-one and 1,3-dimethylbarbituric acid in the presence of N-bromosuccinimide and sodium acetate in EtOH at room temperature was carefully investigated to give novel 1,3-dimethyl-3′,5-diphenyl-1,5-dihydro-2H,5′H-spiro[furo[2,3-d]pyrimi- dine-6,4′-isoxazole]-2,4,5′(3H)-trione in a good yield. The structure of the new compound was confirmed by the results of elemental analysis as well as mass, nuclear magnetic resonance, and infrared spectroscopy.
  Citation: Molbank
  PubDate: 2022-01-14
  DOI: 10.3390/M1317
  Issue No: Vol. 2022, No. 1 (2022)
Molbank, Vol. 2022, Article M1316: Synthesis, Crystal Structure and Cyclic
- Authors: Fatma Aydin, N. Burcu Arslan
  Abstract: Herein, two title compounds, N-benzoyl-N′-(4′-cyanophenyl)thiourea (1) and N-(4-nitrobenzoyl)-N′-(4′-cyanophenyl)thiourea (2) were synthesized in a high yield, via different applications of aroyl isocyanate and 4-aminobenzonitrile. The structure of the prepared compounds was characterized by elemental analysis and FT-IR, 1H, and 13C-NMR spectroscopic methods. The crystal structure of the title compound 1 was determined by an X-ray single-crystal technique and an intramolecular C=O…H-N hydrogen bond and intermolecular C=S…H-N and C=S…H-C hydrogen interactions, which were observed for the crystal structure. The molecular electrostatic potential (MEP) and the Mulliken atomic charges of title compounds 1 and 2 were theoretically calculated and interpreted. Cyclic voltammetric (CV) experiments for the compounds were performed with the glassy carbon electrode. The reduction in potential values of the different functional groups such as nitro and cyano in title compounds were investigated using CV curves.
  Citation: Molbank
  PubDate: 2022-01-14
  DOI: 10.3390/M1316
  Issue No: Vol. 2022, No. 1 (2022)
Molbank, Vol. 2022, Article M1315:
2-(2-(4-Methoxyphenyl)furo[3,2-h]quinolin-3-yl)acetic Acid
- Authors: Boris V. Lichitsky, Andrey N. Komogortsev, Valeriya G. Melekhina
  Abstract: A simple and efficient protocol for the synthesis of the previously unknown 2-(2-(4-methoxyphenyl)furo[3,2-h]quinolin-3-yl)acetic acid was elaborated. The suggested method is based on the telescoped multicomponent reaction of 8-hydroxyquinoline, 4-methylglyoxal, and Meldrum’s acid. The studied process includes the initial interaction of the starting compounds in MeCN followed by intramolecular cyclization to the target product in refluxing acetic acid. The advantage of this approach is the application of readily available starting materials, atom economy, and a simple work-up procedure. The structure of the synthesized furylacetic acid derivative was proven by 1H, 13C, 2D-NMR, IR spectroscopy, and high-resolution mass spectrometry.
  Citation: Molbank
  PubDate: 2022-01-13
  DOI: 10.3390/M1315
  Issue No: Vol. 2022, No. 1 (2022)
Molbank, Vol. 2022, Article M1314:
(E)-1-(3-Benzoyl-4-phenyl-1H-pyrrol-1-yl)-3-phenylprop-2-en-1-one
- Authors: Viola Noti, Dimitra Hadjipavlou-Litina
  Abstract: Over the last decade, there has been an increasing effort to fight inflammatory conditions establishing new multitarget approaches. Chronic inflammation is implicated in many multifactorial diseases, constituting a great economic burden and a chronic health problem. In an attempt to develop new potent multifunctional anti-inflammatory agents, a cinnamic-pyrrole hybrid (6) was synthesized and screened for its antioxidant and anti-Lipoxygenase potential. The new compound, in comparison with its pyrrole precursor (4), showed improved biological activities. In silico calculations were performed to predict its drug-likeness. The examined derivative is considered orally bioavailable according to Lipinski’s rule of five. Compound 6 could be used as a lead for the synthesis of more effective hybrids.
  Citation: Molbank
  PubDate: 2022-01-13
  DOI: 10.3390/M1314
  Issue No: Vol. 2022, No. 1 (2022)
Molbank, Vol. 2022, Article M1313: Synthesis of Flavonoids or Other
Nature-Inspired Small Molecules
- Authors: Giovanni Ribaudo
  Abstract: Natural compounds are endowed with an intriguing variety of scaffolds, functional groups and stereochemical properties [...]
  Citation: Molbank
  PubDate: 2022-01-10
  DOI: 10.3390/M1313
  Issue No: Vol. 2022, No. 1 (2022)