Structural optimization and evaluation of butenolides as potent antifouling agents: modification of the side chain affects the biological activities of compounds

Yongxin Li, Fengying Zhang, Ying Xu, Kiyotaka Matsumura, Zhuang Han, Lingli Liu, Wenhan Lin, Yanxing Jia, Pei-Yuan Qian

Research output: Contribution to journalArticlepeer-review

25 Scopus citations

Abstract

A recent global ban on the use of organotin compounds as antifouling agents has increased the need for safe and effective antifouling compounds. In this study, a series of new butenolide derivatives with various amine side chains was synthesized and evaluated for their anti-larval settlement activities in the barnacle, Balanus amphitrite. Side chain modification of butenolide resulted in butenolides 3c-3d, which possessed desirable physico-chemical properties and demonstrated highly effective non-toxic anti-larval settlement efficacy. A structure-activity relationship analysis revealed that varying the alkyl side chain had a notable effect on anti-larval settlement activity and that seven to eight carbon alkyl side chains with a tert-butyloxycarbonyl (Boc) substituent on an amine terminal were optimal in terms of bioactivity. Analysis of the physico-chemical profile of butenolide analogues indicated that lipophilicity is a very important physico-chemical parameter contributing to bioactivity. © 2012 Copyright Taylor and Francis Group, LLC.
Original languageEnglish (US)
Pages (from-to)857-864
Number of pages8
JournalBiofouling
Volume28
Issue number8
DOIs
StatePublished - Aug 24 2012
Externally publishedYes

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