“Anti-Michael” and Michael Additions in the Reactions of 2-Arylmethyliden-1,3-Indandiones with 2-Aminothiophenol

• 作者: a Alberto D. Herná Elena I. Klimova Elena Martí Jessica J. Sá Marcos Flores-Alamo nchez Garcí ndez-Suzan nez-Klimova rez Apan Teresa Ramí
• 来源期刊: 有机化学国际期刊(英文)
• 学科: 化学
• 关键词: FERROCENE Addition “Anti-Michael” Reaction CYCLIZATION 1 5-Thiazepines 4-Thiazines Antitumor Cell Lines
• 年，卷（期）: 2017,（1）
• 页码范围: 57-81
• 页数: 25页
• 分类号: O6

摘要

A novel 2-indano[2,3b]-2-ferrocenyl- and 2-indano[2,3b]-2-(p-methoxy-phenyl)[1,5]benzo-2,5-dihydrothiazepine 5a,b (addition Michael/cyclization) (~30.32%), indano[2,3b]-2-ferrocenyl- and 2-(p-methoxyphenyl)[1,4] benzothiazine 4a,b (addition “anti-Michael”/cyclization) (~45.43%), respectively, were obtained by the condensation of 2-ferrocenyl-and 2-(p-methoxy-phenyl)methyliden-1,3-indandiones 1a,b with o-aminothiophenol 2 in the presence of AcOH and HCl. A new “anti-Michael” addition reaction of 1,4-bis-heteronucleophile 2 into 2-arylmethyliden-1,3-indandiones was reported. As a result of this reaction the product 1a,b was obtained. The structures of the resultant compounds were elucidated by IR, 1H and 13C NMR spectroscopy, mass spectrometry, elemental and X-ray diffraction analysis. The in vitro antitumor activity of the obtained products was researched using the following human cancer cell lines: glioblastoma (CNS U-251), prostatic adenocarcinoma (PC-3), chronic myelogenous leukemia (K562), colorectal adenocarcinoma (HCT-15), mammary adenocarcinoma (MCF-7), and small cell lung cancer (SKLU) and the sulforhodamine B (SRB) method. Among these new compounds some thiazine and thiazepine derivatives showed compelling in vitro antitumor effects on cell lines K-562, HCT-15, SKLU-1 and MCF-7.