Facile synthesis, spectral characterization, antimicrobial and in vitro cytotoxicity of novel N3,N5-diisonicotinyl-2,6-dimethyl-4-phenyl-1,4-dihydropyridine-3,5-dicarbohydrazide derivatives

AbstractA new series of some novel isoniazid condensed 1,4-dihydropyridines was prepared by reaction of N-(3-oxobutanoyl) isonicotinohydrazide with aryl aldehyde and 25–30% ammonia solution in the presence of catalytic amount of barium nitrate as an efficient catalyst. The confirmation of the chemical structure of the synthesized compounds (4a–m) was substantiated by TLC, different spectral data IR, 1H NMR, 13C NMR, and mass spectra and elemental analysis was done. The synthesized compounds were evaluated for antimicrobial activity and cytotoxicity against Gram-positive bacteria Bacillus subtilis, Gram-negative bacteria Escherichia coli and Vero cells. All the reported compounds exhibited weak, moderate, or high antimicrobial activity and cytotoxicity. Especially, compound 4i showed the best antimicrobial activity and cytotoxicity of all the 1,4-dihydropyridine derivatives, with an MIC value of 11.5μM, 12.2μM and a CTC50 value of 27μM

Ethyl 4-anilino-3-nitro­benzoate

In the title compound, C15H14N2O4, the dihedral angle between the benzene and phenyl rings is 73.20 (6)°. An intra­molecular N—H⋯O hydrogen bond forms an S(6) ring motif. In the crystal, mol­ecules are linked by N—H⋯O and C—H⋯O hydrogen bonds into a layer parallel to the bc plane

Ethyl 2-(4-chloro­phen­yl)-1-phenyl-1H-benzimidazole-5-carboxyl­ate

In the title compound, C22H17ClN2O2, the essentially planar benzimidazole ring system [maximum deviation = 0.012 (2) Å] forms dihedral angles of 28.69 (6) and 63.65 (7)°, respectively, with the phenyl and chloro-substituted benzene rings. The dihedral angle between the phenyl and benzene rings is 64.23 (8)°. In the crystal, mol­ecules are linked into a zigzag chain along the a axis by inter­molecular C—H⋯O hydrogen bonds. C—H⋯π inter­actions are also present

Novel isoniazid cyclocondensed 1,2,3,4-tetrahydropyrimidine derivatives for treating infectious disease: a synthesis and in vitro biological evaluation

Objective: To synthesize new congeners by incorporating isoniazid with 1,2,3,4-tetrahydropyrimidinones moieties in a single molecular frame work and to evaluate their antimicrobial and antimycobacterial activity. Methods: A new series of some novel isoniazid cyclocondensed 1,2,3,4-tetrahydropyrimidines was prepared by N′-acetoacetylisonicotinohydrazide with urea/thiourea and appropriate aldehyde in the presence of catalytic amount of laboratory made benzenesulphonic acid. Confirmation of the chemical structure of the synthesized compounds (4a-n) was substantiated by melting point, TLC, different spectral data IR, 1H-NMR, and Mass spectra were done. The synthesized compounds were evaluated for in vitro antimicrobial and antimycobacterial activity against Bacillus subtilis (B. subtilis), Escherichia coli (E. coli), Mycobacterium tuberculosis (M. tuberculosis) CIP and H37Rv strain. Results: The titled compounds exhibited weak, moderate, or high antimicrobial and antimycobacterial activity. Compounds 4l, 4m, and 4n, exhibited potential antimicrobial and antimycobacterial action, when compare with the current therapeutic agent of Norfloxacin and Rifampicin. Conclusions: Compound 4l, 4m, and 4n is arguably the most potent, our present study makes it an interesting compound when compared to the current therapeutic agents and are considered the candidates to investigate further for the same

Antimicrobial and in vitro cytotoxicity of novel sulphanilamide condensed 1,2,3,4-tetrahydropyrimidines

The purpose of the study was to synthesize potent antimicrobial and cytotoxic agents by condensing sulphanilamide with 1,2,3,4-tetrahydropyrimidines. A new series of novel sulphanilamide condensed 1,2,3,4-tetrahydropyrimidines was prepared by reacting N-[(4-aminophenyl) sulphonyl]-3-oxobutanamide with urea/thiourea and aryl aldehyde in the presence of a catalytic amount of laboratory prepared chlorosulphonic acid as an efficient catalyst. The chemical structures of the synthesized compounds (7a-r) were confirmed by TLC, and the compounds were characterized by IR, 1H NMR, mass spectra and elemental analysis. The synthesized compounds were evaluated for antimicrobial activity against the Gram-positive bacteria Bacillus subtilis and the Gram-negative bacteria Escherichia coli and for cytotoxicity against Vero cells. These compounds exhibited weak, moderate, or high antimicrobial activities and cytotoxicity. In particular, compound 7p exhibited the best antimicrobial activity and cytotoxicity of all the 1,2,3,4-tetrahydropyrimidine derivatives with antimicrobial activity MIC values of 11.4 μM and 12.1 μM against B. subtilis and E. coli, respectively, and a cytotoxicity CTC50 value of 19.0 μM against Vero cells. The sulphanilamide condensed 1,2,3,4-tetrahydropyrimidines generated here might prove interesting as potential antimicrobial cytotoxic agents

Acetylcholinesterase enzyme inhibitor activity of some novel pyrazinamide condensed 1,2,3,4-tetrahydropyrimidines

AbstractA new series of some novel pyrazinamide condensed 1,2,3,4-tetrahydropyrimidines was prepared by reacting of N-(3-oxobutanoyl)pyrazine-2-carboxamide with urea/thiourea and appropriate aldehyde in the presence of catalytic amount of laboratory made p-toluenesulfonic acid as an efficient catalyst. Confirmation of the chemical structure of the synthesized compounds (4a–l) was substantiated by TLC, different spectral data IR, 1H NMR, mass spectra and elemental analysis. The synthesized compounds were evaluated for acetyl and butyl cholinesterase (AChE and BuChE) inhibitor activity. The titled compounds exhibited weak, moderate or high AChE and BuChE inhibitor activity. Especially, compound (4l) showed the best AChE and BuChE inhibitory activity of all the 1,2,3,4-tetrahydropyrimidine derivatives, with an IC50 value of 0.11μM and 3.4μM

Microwave assisted synthesis of some novel acetazolamide cyclocondensed 1,2,3,4-tetrahydropyrimidines as a potent antimicrobial and cytotoxic agents

A new series of some novel acetazolamide cyclocondensed 1,2,3,4-tetrahydropyrimidines was prepared by reacting of N-{[5-(acetylamino)-1,3,4-thiadiazol-2-yl]sulfonyl}-3-oxobutanamide with urea/thiourea and appropriate aldehyde in the presence of catalytic amount of laboratory made p-toluenesulfonic acid as an efficient catalyst. Confirmation of the chemical structure of the synthesized compounds (12a–n) was substantiated by TLC, different spectral data IR, 1H NMR, Mass spectra and elemental analysis were done. The synthesized compounds were evaluated for in-vitro antimicrobial and cytotoxicity against Bacillus subtilis, Escherichia coli and Vero cells. The titled compounds exhibited weak, moderate, or high in-vitro antimicrobial and cytotoxicity. Compounds 12c, 12d, 12g and 12h, exhibited potential antimicrobial and in-vitro cytotoxicity

Substituted spiro [2.3'] oxindolespiro [3.2″]-5,6-dimethoxy-indane-1″-one-pyrrolidine analogue as inhibitors of acetylcholinesterase

Series of pyrolidine analogues were synthesized and examined as acetylcholinesterase (AChE) inhibitors. Among the compounds, compounds 4k and 6k were the most potent inhibitors of the series. Compound 4k, showed potent inhibitory activity against acetyl cholinesterase enzyme with IC(50) 0.10 μmol/L. Pyrolidine analogues might be potential acetyl cholinesterase agents for AD

Synthesis and discovery of novel hexacyclic cage compounds as inhibitors of acetylcholinesterase

Hexacyclic derivatives share vital pharmacological properties, considered useful in Alzheimer's disease. The aim of this study was synthesis and its evaluation for acetyl cholinesterase inhibitory activity of novel hexacyclic analogues. Compound 4f, showed potent inhibitory activity against acetyl cholinesterase enzyme with IC(50) 0.72 μmol/L