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] benzo...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.展开更多
A highly stereoselective asymmetric cascade cyclization reaction between o-hydroxycinnamaldehydes and diphenylphosphine oxide has been achieved with 84%-99% ee and 7：1-20：1 dr under the catalysis of L-diarylprolinol...A highly stereoselective asymmetric cascade cyclization reaction between o-hydroxycinnamaldehydes and diphenylphosphine oxide has been achieved with 84%-99% ee and 7：1-20：1 dr under the catalysis of L-diarylprolinol silyl ether. This reaction provides a facile access to highly enantioenriched 4- diphenylphosphinyl chroman-2-ols. It also represents a novel organocatalytic asymmetric phospha- Michael addition of α,β-unsaturated aldehydes with pentavalent P-nucleophiles.展开更多
文摘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.
基金Financial support from the National Natural Science Foundation of China(Nos. 21472096, J1103306)
文摘A highly stereoselective asymmetric cascade cyclization reaction between o-hydroxycinnamaldehydes and diphenylphosphine oxide has been achieved with 84%-99% ee and 7：1-20：1 dr under the catalysis of L-diarylprolinol silyl ether. This reaction provides a facile access to highly enantioenriched 4- diphenylphosphinyl chroman-2-ols. It also represents a novel organocatalytic asymmetric phospha- Michael addition of α,β-unsaturated aldehydes with pentavalent P-nucleophiles.
