1,3-Dipolar cycloaddition enabled isoxazole-fused spiropyrrolidine oxindoles syntheses from 3-methyl-4-nitro-5-alkenyl-isoxazoles and azomethine ylides

Add time:09/01/2019    Source:sciencedirect.com

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.

We also recommend Trading Suppliers and Manufacturers of 3,5-DiMethyl-4-(2-nitrophenyl)isoxazole (cas 136295-82-4). Pls Click Website Link as below: cas 136295-82-4 suppliers

Prev:Three multicomponent reactions of 3,5-dimethyl-4-nitroisoxazole
Next:Synthesis and SAR of new isoxazole-triazole bis-heterocyclic compounds as analogues of natural lignans with antiparasitic activity)