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

Authors

Sarah Yong, University of WollongongFollow
Alison T. Ung, University of WollongongFollow
Stephen G. Pyne, University of WollongongFollow
Brian W. Skelton, University of Western Australia
Allan H. White, University of Western Australia

RIS ID

19188

Publication Details

Yong, S., Ung, A. T., Pyne, S. G., Skelton, B. W. & White, A. H. (2007). Synthesis of novel 3''-spirocyclic-oxindole derivatives and assessment of their cytostatic activities. Tetrahedron, 63 5579-5586.

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 heterocyclic structures, is described. These compounds were prepared from methyl α-(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 GI₅₀ values of 2.6–4.1 μM on the human breast cancer cell line, MCF-7.