Solid‐phase Total Synthesis of Amide Analogues of Coibamide A: Azacoibamide A and O‐Desmethyl Azacoibamide A

Bulletin of the Korean Chemical Society

Jaekwan Park¹  Jeong Lim¹  Dongyeol Lim²  Soo‐³  Ganesh A. Sable³ 

[1] 747 Republic of Korea;Department of Bioscience and Biotechnology Sejong University Seoul 143‐Department of Chemistry Sejong University Seoul 143‐

关键词: Solid‐;    phase synthesis;    Coibamide A;    Azacoibamide A;    On‐;    resin cyclization;    O‐;    Methylation;   

DOI  :  10.1002/bkcs.10674

学科分类：化学（综合）

来源: Korean Chemical Society

【 摘 要 】

Solid‐phase total syntheses of highly methylated cyclic azacoibamide A and its O‐desmethyl analogue were achieved. Two ester linkages of natural coibamide A were replaced by amide bonds to improve its pharmacokinetic properties. The synthetic strategy consists of the key on‐resin macrocyclization, N,N‐dimethylation, and final solution phase O‐methylation reactions. Compared to the naturally occurring coibamide A, azacoibamide A and its O‐desmethyl analogue displayed low micromolar activities against tested cancer cell lines.

【 授权许可】

Unknown