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http://ir.nhri.org.tw/handle/3990099045/1119
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| Title: | Synthesis, antiproliferative, and vasorelaxing evaluations of coumarin alpha-methylene-gamma-butyrolactones |
| Authors: | Chen, YL;Lu, CM;Lee, SJ;Kuo, DH;Chen, IL;Wang, TC;Tzeng, CC |
| Contributors: | Division of Biotechnology and Pharmaceutical Research |
| Abstract: | Certain coumarin alpha-methylene-gamma-butyrolactones were synthesized and evaluated for antiproliferative and vasorelaxing activities. These compounds were synthesized via alkylation of hydroxycoumarins 2a-f followed by oxidation and the Reformatsky-type condensation. The results of this study are as follows (1) for the vasorelaxing activity, coumarin-7-yl alpha-methylene-gamma-butyrolactone 6d, with an IC50 value of 9.4 mu M against pig coronary arterial contraction induced by KCl, is a more active vasorelaxant than its coumarin-4-yl counterpart 6a and its gamma-methyl congener 1. A methyl group substituted at C-4 of the coumarin-7-yl moiety reduced the vasorelaxing effect (6d vs 6e) while the 3,4,8-trimethyl derivative 6f was inactive. (2) For the antiproliferative activity, coumarin-4-yl alpha-methylene-gamma-butyrolactone 6a, which exhibited the most potent antiproliferative activity on the growth of MCF7, NCI-H460, and SF-268 with IC50 values of 6.97, 14.68, and 8.36 mu M, respectively, is more cytotoxic than its coumarin-7-yl counterpart 6d and the 6,7-dimethyl derivative 6b. For the coumarin-7-yl derivatives, 6d is more active than its gamma-methyl congener 1, indicating that substitution at the gamma-position decreased cytotoxicity. (c) 2005 Elsevier Ltd. All rights reserved. |
| Keywords: | Biochemistry & Molecular Biology;Chemistry, Medicinal;Chemistry, Organic |
| Date: | 2005-10-15 |
| Relation: | Bioorganic and Medicinal Chemistry. 2005 Oct;13(20):5710-5716. |
| Link to: | http://dx.doi.org/10.1016/j.bmc.2005.06.013 |
| JIF/Ranking 2023: | http://gateway.webofknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcAuth=NHRI&SrcApp=NHRI_IR&KeyISSN=0968-0896&DestApp=IC2JCR |
| Cited Times(WOS): | https://www.webofscience.com/wos/woscc/full-record/WOS:000231933200003 |
| Cited Times(Scopus): | http://www.scopus.com/inward/record.url?partnerID=HzOxMe3b&scp=24344471025 |
| Appears in Collections: | [李秀珠] 期刊論文
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| 000231933200003.pdf | | 199Kb | Adobe PDF | 643 | View/Open |
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