Title: Synthesis and Cytotoxicity Evaluation of Certainα-Methylidene-γ-butyrolactones Bearing Coumarin, Flavone, Xanthone, Carbazole, and Dibenzofuran Moieties
Abstract: Helvetica Chimica ActaVolume 83, Issue 5 p. 989-994 Research ArticleFull Access Synthesis and Cytotoxicity Evaluation of Certain α-Methylidene- γ-butyrolactones Bearing Coumarin, Flavone, Xanthone, Carbazole, and Dibenzofuran Moieties Yeh-Long Chen, Yeh-Long Chen School of Chemistry, Kaohsiung Medical University, Kaohsiung 807, TaiwanSearch for more papers by this authorI-Li Chen, I-Li Chen School of Chemistry, Kaohsiung Medical University, Kaohsiung 807, TaiwanSearch for more papers by this authorCherng-Chyi Tzeng, Cherng-Chyi Tzeng School of Chemistry, Kaohsiung Medical University, Kaohsiung 807, TaiwanSearch for more papers by this authorTai-Chi Wang, Tai-Chi Wang Department of Pharmacy, Tajen Institute of Technology, Pingtung 907, TaiwanSearch for more papers by this author Yeh-Long Chen, Yeh-Long Chen School of Chemistry, Kaohsiung Medical University, Kaohsiung 807, TaiwanSearch for more papers by this authorI-Li Chen, I-Li Chen School of Chemistry, Kaohsiung Medical University, Kaohsiung 807, TaiwanSearch for more papers by this authorCherng-Chyi Tzeng, Cherng-Chyi Tzeng School of Chemistry, Kaohsiung Medical University, Kaohsiung 807, TaiwanSearch for more papers by this authorTai-Chi Wang, Tai-Chi Wang Department of Pharmacy, Tajen Institute of Technology, Pingtung 907, TaiwanSearch for more papers by this author First published: 04 May 2000 https://doi.org/10.1002/(SICI)1522-2675(20000510)83:5<989::AID-HLCA989>3.0.CO;2-ECitations: 31AboutPDF ToolsRequest permissionExport citationAdd to favoritesTrack citation ShareShare Give accessShare full text accessShare full-text accessPlease review our Terms and Conditions of Use and check box below to share full-text version of article.I have read and accept the Wiley Online Library Terms and Conditions of UseShareable LinkUse the link below to share a full-text version of this article with your friends and colleagues. Learn more.Copy URL Share a linkShare onEmailFacebookTwitterLinkedInRedditWechat Abstract The cytotoxicities of α-methylidene-γ-butyrolactones, which are linked to coumarins (see 15 and 16) and to potential DNA-intercalating carriers such as flavones, xanthones, carbazole, and dibenzofuran (see 9a – e, 10a – e, 11, and 12), were studied. These compounds were synthesized via alkylation of their hydroxy precursors followed by a Reformatsky-type condensation (Scheme). These α-methylidene-γ-butyralactones were evaluated in vitro against 60 human tumor cell lines derived from nine cancer cell types and demonstrated a strong growth-inhibitory activity against leukemia cancer cells (Tables 1 and 2). For flavone- and xanthone-containing α-methylidene-γ-butyrolactones 9a – e and 10a – e, respectively, the overall potency (mean value) decreased on introduction of an electron-withdrawing substituent at the γ-phenyl substituent and increased with an electron-donating substituent. Comparing the different chromophores established the following order of decreasing potency (log GI50): dibenzofuran (12, −6.17) > flavone (9a, −5.96) > carbazole (11, −5.80) and xanthone (10a, −5.77) > coumarin (15, −5.60; 16, −5.65). Among them, the dibenzofuran derivative 12 showed not only strong inhibitory activities against leukemia cancer cell lines with an average log GI50 value of −7.22, but also good inhibitory activities against colon, melanoma, and breast cancer cells with average log GI50 values of −6.23, −6.31, and −6.39, respectively. Citing Literature Volume83, Issue5May 10, 2000Pages 989-994 RelatedInformation