Synthesis of novel 3'-spirocyclic-oxindole derivatives and assessment of their cytostatic activities

S.R. Yong, A.T. Ung, S.G. Pyne, Brian Skelton, Allan White

Research output: Contribution to journalArticle

57 Citations (Scopus)

Abstract

The synthesis of some novel 3'-spirocyclic-oxindole compounds, based on the spiro[indole-3,5'-isoxazolidin]-2(1H)-one, the 2'H-spiro[indole-3,6'-[1,3]oxazinane]-2,2'(1H)-dione and the 2'H-spiro[indoline-3,3'-pyrrolo[1,2-c][1,3']oxazine]-1',2(1H)-dione hetero-cyclic structures, is described. These compounds were prepared from methyl alpha-(2-nitrophenyl)acrylate via [1,3]-dipolar cycloaddition reactions with two acyclic nitrones and one cyclic nitrone followed by reduction of the cycloadducts and then treatment with triphosgene. Two of these compounds showed significant cytostatic activity on three cancer cell lines with GI(50) values of 2.6-4.1 mu M on the human breast cancer cell line, MCF-7. Crown Copyright (c) 2007 Published by Elsevier Ltd. All rights reserved.
Original languageEnglish
Pages (from-to)5579-5586
JournalTetrahedron
Volume63
Issue number25
DOIs
Publication statusPublished - 2007

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