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- Publisher Website: 10.1080/08927014.2012.717071
- Scopus: eid_2-s2.0-84865540117
- PMID: 22920194
- WOS: WOS:000313001100006
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Article: Structural optimization and evaluation of butenolides as potent antifouling agents: Modification of the side chain affects the biological activities of compounds
Title | Structural optimization and evaluation of butenolides as potent antifouling agents: Modification of the side chain affects the biological activities of compounds |
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Authors | |
Keywords | anti-larval settlement lipophilicity butenolides barnacle antifouling side chain modification structural optimization |
Issue Date | 2012 |
Citation | Biofouling, 2012, v. 28, n. 8, p. 857-864 How to Cite? |
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. |
Persistent Identifier | http://hdl.handle.net/10722/273496 |
ISSN | 2021 Impact Factor: 3.797 2020 SCImago Journal Rankings: 0.668 |
ISI Accession Number ID |
DC Field | Value | Language |
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dc.contributor.author | Li, Yongxin | - |
dc.contributor.author | Zhang, Fengying | - |
dc.contributor.author | Xu, Ying | - |
dc.contributor.author | Matsumura, Kiyotaka | - |
dc.contributor.author | Han, Zhuang | - |
dc.contributor.author | Liu, Lingli | - |
dc.contributor.author | Lin, Wenhan | - |
dc.contributor.author | Jia, Yanxing | - |
dc.contributor.author | Qian, Pei Yuan | - |
dc.date.accessioned | 2019-08-12T09:55:45Z | - |
dc.date.available | 2019-08-12T09:55:45Z | - |
dc.date.issued | 2012 | - |
dc.identifier.citation | Biofouling, 2012, v. 28, n. 8, p. 857-864 | - |
dc.identifier.issn | 0892-7014 | - |
dc.identifier.uri | http://hdl.handle.net/10722/273496 | - |
dc.description.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. | - |
dc.language | eng | - |
dc.relation.ispartof | Biofouling | - |
dc.subject | anti-larval settlement | - |
dc.subject | lipophilicity | - |
dc.subject | butenolides | - |
dc.subject | barnacle | - |
dc.subject | antifouling | - |
dc.subject | side chain modification | - |
dc.subject | structural optimization | - |
dc.title | Structural optimization and evaluation of butenolides as potent antifouling agents: Modification of the side chain affects the biological activities of compounds | - |
dc.type | Article | - |
dc.description.nature | link_to_subscribed_fulltext | - |
dc.identifier.doi | 10.1080/08927014.2012.717071 | - |
dc.identifier.pmid | 22920194 | - |
dc.identifier.scopus | eid_2-s2.0-84865540117 | - |
dc.identifier.volume | 28 | - |
dc.identifier.issue | 8 | - |
dc.identifier.spage | 857 | - |
dc.identifier.epage | 864 | - |
dc.identifier.eissn | 1029-2454 | - |
dc.identifier.isi | WOS:000313001100006 | - |
dc.identifier.issnl | 0892-7014 | - |