期刊
TETRAHEDRON
卷 72, 期 10, 页码 1364-1374出版社
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2016.01.029
关键词
1,3-Dipolar cycloaddition reaction; 3-Methyl-4-nitro-5-alkenyl-isoxazoles; Azomethine ylides; Isoxazole-fused spiropyrrolidine oxindoles; Antitumor activity
资金
- National Natural Science Foundation of China [21302024, 81560563]
- Excellent creative talents of science and technology support plan in Guizhou Province Colleges and Universities [(2015) 491]
- Guizhou Teaching Reform Project [SJJG201423]
- Guizhou University Innovation Fund [2015023]
- Mutual Funds of Guizhou Province and Guizhou University [[2014]7662]
A facile and efficient methodology was developed for the synthesis of isoxazole-fused spiropyrrolidine oxindoles 3-5 via a 1,3-dipolar cycloaddition reaction of 3-methyl-4-nitro-5-alkenyl-isoxazoles with azomethine ylides (thermally generated in situ from isatin derivatives and proline or thioproline or sarcosine). Products bearing adjacent quaternary-tertiary centers were smoothly obtained in high yields (up to 90% yield) with good diastereoselectivity (up to 20:1). Furthermore, their biological activity has been preliminarily demonstrated by in vitro evaluation against human prostate cancer cells PC-3, human lung cancer cells A549 and human leukemia cells K562 by the MTT-based assays using the commercially available standard drug Cisplatin as a positive control. These results suggested that most of isoxazole-fused spiropyrrolidine oxindoles 3-5 showed considerable cytotoxicities to these three cell lines K562, A549 and PC-3, and that isoxazole-fused spiropyrrolidine oxindoles may be potential leads for further biological screening. (C) 2016 Elsevier Ltd. All rights reserved.
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