期刊
MEDICINAL CHEMISTRY
卷 7, 期 6, 页码 561-571出版社
BENTHAM SCIENCE PUBL LTD
DOI: 10.2174/157340611797928307
关键词
TMSCl-NaI-MeCN; cyclization; benzo[e][1,2]thiazines; benzosultams; MCF-7 cells; anticancer
资金
- National Natural Science Foundation of China (NSFC) [30873134]
- Natural Science Foundation of Shandong Province [Y2007C125]
A practical synthesis of 2,3-diarylated 2H-benzo[e][1,2]thiazine 1,1-dioxides and their 3,4-dihydro derivatives was developed. ortho-Methyl lithiation of N-aryl-o-toluenesulfonamide followed by reaction with aryl aldehydes gave carbinol sulfonamides, which were either converted directly, or first oxidized to their ketones and converted, to 2,3-diarylated six-membered benzosultams via a TMSCl-NaI-MeCN mediated cyclization. A library of benzosultams was synthesized and evaluated for inhibitory activity against MCF-7 cells. Compound 3 in the 3,4-dihydro (saturated) series and compound 8 in the unsaturated series exhibited the highest potencies with growth inhibition (GI(50)) values of 0.8 and 18.0 mu M, respectively. Molecular modeling studies suggest that these compounds can associate with the colchicine binding site on microtubules. However, experimental assessments of that and other mechanistic possibilities are still ongoing.
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