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Rapid synthesis and bioactivities of 3-(nitromethylene)indolin-2-one analogues

✍ Scribed by Gang Chen; Xiao-Jiang Hao; Qian-Yun Sun; Jian Ding

Book ID
111491382
Publisher
Versita
Year
2010
Tongue
English
Weight
210 KB
Volume
64
Category
Article
ISSN
0366-6352

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✦ Synopsis

Abstract

A new synthesis method of 3-(nitromethylene)indolin-2-one analogues is described, using the Henry reaction of isatin and N-substituted isatins with nitromethane followed by dehydration of the nitroaldol adduct with mesyl chloride. The use of diethylamine (rather than DBU) as the base catalyst in a solvent-free Henry reaction gave the nitroaldol adduct in sufficient purity as to allow its direct dehydration to nitroalkene. Overall yields for this two-step synthesis are satisfactory (typically 50–77 % after chromatographic purification). 3-(Nitromethylene)indolin-2-one analogues are valued protective agents against H2O2-induced apoptosis using PC12 cells, and for their cytotoxicity against the A549 and P388 lung cancer cell lines. One compound, (E)-1-benzyl-3-(nitromethylene)indolin-2-one (VIII), exhibited potent activity in the latter assay.

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## Abstract magnified image A series of propargylic alcohol was synthesized by the addition of phenylacetylene to isatin and its N‐substituted derivatives for the first time. This reaction involves activation of zinc reagent __via__ coordination with carbonyl substrates that behave β€œligand like.”