Insights into the structure–activity relationship of the anticancer compound ZJ-101: A critical role played by the cyclohexene ring. Issue 12 (15th June 2016)

• Record Type: Journal Article
• Authors: Shah, Aashay K.; Qian, Shan; Zhang, Dawei; Head, Sarah A.; Liu, Jun O.; Jin, Zhendong
• Is Part Of: Bioorganic & medicinal chemistry letters. Volume 26:Issue 12(2016)
• Page Start: 2890
• Page End: 2892
• Publication Date: 2016-06-15
• Subjects: Superstolide A analog -- Anticancer agent -- Structure–activity relationship -- Drug design -- Asymmetric synthesis; Bioorganic chemistry -- Periodicals; Pharmaceutical chemistry -- Periodicals; 572
• DOI: 10.1016/j.bmcl.2016.04.044
• Languages: English
• ISSNs: 0960-894X

Abstract

Graphical abstract: Abstract: Compound ZJ-101, a structurally simplified analog of the marine natural product superstolide A, was previously developed in our laboratory. In the subsequent structure–activity relationship study, a new analog ZJ-102 was designed and synthesized to probe the importance of the cyclohexenyl group through its replacement to a phenyl group using a concise and convergent synthetic approach. The biological evaluation showed that this new analog ZJ-102 is significantly less active against cancer cells in vitro than ZJ-101, suggesting that the cyclohexenyl ring (along with its two stereogenic centers) present in ZJ-101 is important for its anticancer activity.