Synthesis of Secondary and Tertiary Oxime Carbamate Derivatives and their Structure‐Dependent Bioactivity

Bulletin of the Korean Chemical Society

Venugopal Thanikachalam¹  Bong‐²  Rajamanickam Sivakumar²  Gi Kim² 

[1] Department of Chemistry Annamalai University Chidambaram 608 002 Tamil Nadu India;Department of Organic and Nano System Engineering Konkuk University Seoul 05029 Korea

关键词: Oxime carbamate;    Structure‐;    dependent bioactivity;    Organic synthesis;    Cyclohexylisocyanate;    1,1′;    ‐;    Carbonyldiimidazole;   

DOI  :  10.1002/bkcs.11159

学科分类：化学（综合）

来源: Korean Chemical Society

【 摘 要 】

Biologically active novel piperidin‐4‐one oxime carbamates were synthesized from 3‐ethyl‐1‐methyl‐2,6‐diphenylpiperidin‐4‐one oxime, 1,1′‐carbonyldiimidazole (CDI), and primary or secondary amines in the presence of sodium hydride as base. Commercially available, cheaper, and safer CDI was utilized as carbonyl source, instead of toxic phosgene/triphosgene and carbon monoxide. The devised method is feasible for primary and secondary amines to make their corresponding oxime carbamate derivatives, through oxime–imidazolide intermediate, in high yield. When the antimicrobial activity of obtained oxime carbamate derivatives was investigated in comparison with streptomycin and amphotericin B as standards, the oxime carbamate containing heteroaromatic thiazole ring exhibits outstanding antimicrobial effectiveness, regardless of bacterial or fungal types.

【 授权许可】

Unknown