Design, Synthesis, Biological and Molecular Docking Studies of Some O-Hydroxycyanopyridine Derivatives

A series of O- and N-alkylated 2-pyridone derivatives 2a-c-8a,b were obtained from alkylation of 1a-c with different alkylating agents. Hydrazonolysis of 7a,b followed by reaction with aromatic aldehydes and active methylene reagents affroded the hydrazones 10a,b, 11a,b and 13, in addition to, pyrazole derivative 12. While, the hydrazide 14a,b obtained from hydrazonolysis of the ester 8a,b followed by reaction with ethyl acetoacetate and p-aminoacetophenone to give the corresponding hydrazones 15 and 16, respectively. Diazitization of 1b followed by reaction with active methylene reagents afforded hydrazonid derivatives 17 and 18. Sulpha-drugs 21-23 were obtained from alkylation of 2-thiooxopyridone 19 with chloroacetic acid followed by reaction with different sulphonamide derivatives. The triazole derivatives containing 2-pyridone moiety 24-26 were obtained from the reaction of 2a-c with ethyl 3-azidopropanoate via click reaction. All the newly synthesized compounds are elucidated by spectroscopic data (IR, 1H, 13C NMR, Mass spectrometry and elemental analyses. Some of these compounds evaluated against anti-cancer, antioxidant and antimicrobial and give a good and moderate effect.

Author(s): Ahmed H Moustafa, Nermin A M El-Seadawy, Allam A Hassan, Shirin H Pasha, Hassan A El-Sayed, Nadia A M Shimess, Nasser A Hassan

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