Synthesis, biological and computational study of new Schiff base hydrazones bearing 3-(4-pyridine)-5-mercapto-1,2,4-triazole moiety.
A series of new Schiff base hydrazones (compounds 1-16) were synthesized by condensation reaction of 4-amino-3-(4-pyridine)-5-mercapto-1,2,4-triazole with various aldehydes and/or dialdehydes. The structure of the prepared compounds was confirmed by means of 1H NMR, 13C NMR, UV-vis, IR and elemental analyses. The all prepared compounds were assayed for antibacterial (Escherichia coli and Staphylococcus aureus) and antifungal (Candida albicans) activities by disc diffusion method. The results indicate that all tested compounds did not show any antibacterial activity against E. coli, as gram negative bacteria, and antifungal activity against C. albicans. But the compounds 2, 3, 4, 6 and 8 containing 4-Cl, 4-Me, 4-MeO, 2,4-di-Cl and 2-OH substituted phenyl moiety, respectively, showed good inhibition against S. aureus as compare to standard drugs. The structure of all biologically active compounds has also been theoretically studied by ab initio Hartree-Fock (HF) methods.
Khanmohammadi
Hamid
H
Department of Chemistry, Arak University, Arak 38156, Iran. h-khanmohammadi@araku.ac.ir
Abnosi
Mohammad H
MH
Hosseinzadeh
Ali
A
Erfantalab
Malihe
M
D000890:Anti-Infective Agents / Q000494:pharmacology; D002176:Candida albicans / Q000378:metabolism; D002626:Chemistry, Pharmaceutical / Q000379:methods*; D015195:Drug Design; D004563:Electrochemistry; D004926:Escherichia coli / Q000378:metabolism; D006835:Hydrazones / Q000138:chemical synthesis / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D008956:Models, Chemical; D008968:Molecular Conformation; D012545:Schiff Bases / Q000138:chemical synthesis / Q000737:chemistry*; D013056:Spectrophotometry, Ultraviolet / Q000379:methods; D013211:Staphylococcus aureus / Q000378:metabolism; D014230:Triazoles / Q000737:chemistry*; D014961:X-Ray Diffraction
D000890:Anti-Infective Agents; D006835:Hydrazones; D012545:Schiff Bases; D014230:Triazoles