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  • Title: Structural optimization and evaluation of butenolides as potent antifouling agents: modification of the side chain affects the biological activities of compounds.
    Author: Li Y, Zhang F, Xu Y, Matsumura K, Han Z, Liu L, Lin W, Jia Y, Qian PY.
    Journal: Biofouling; 2012; 28(8):857-64. PubMed ID: 22920194.
    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.
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