Structure–activity relationship study of syringolin A as a potential anticancer agent. Issue 21 (1st November 2015)

• Record Type: Journal Article
• Authors: Chiba, Takuya; Matsuda, Akira; Ichikawa, Satoshi
• Is Part Of: Bioorganic & medicinal chemistry letters. Volume 25:Issue 21(2015)
• Page Start: 4872
• Page End: 4877
• Publication Date: 2015-11-01
• Subjects: Fmoc 9-fluorenylmethyloxycarbonyl -- EDCI 1-ethyl-3-(3-dimethylaminopropyl)carboxamide -- HOBt 1-hydroxybenzotriazole -- DMF N, N-dimethylformamide; Proteasome inhibitor -- Cancer -- Structure–activity relationship; Bioorganic chemistry -- Periodicals; Pharmaceutical chemistry -- Periodicals; 572
• DOI: 10.1016/j.bmcl.2015.06.015
• Languages: English
• ISSNs: 0960-894X

Abstract

Graphical abstract: Abstract: A detailed structure–activity relationship of syringolin A (1 ), which is a promising antitumor natural product, was described. We previously developed syringolin A analog2 as a potent proteasome inhibitor by the structure-based drug design of syringolin A. In this Letter, we synthesized a range of analogs of2, having a different length of the lipophilic chain and substituted aryl group, and their cytotoxicity against human cancer cells was evaluated. It turned out that these modifications greatly affected the cytotoxicity. Further optimization would lead to develop a novel proteasome inhibitor.