Synthesis of novel 3′-spirocyclic-oxindole derivatives and assessment of their cytostatic activities |
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Authors: | Sarah R Yong Stephen G Pyne Brian W Skelton |
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Institution: | a Department of Chemistry, University of Wollongong, Wollongong, New South Wales 2522, Australia b Department of Chemistry, University of Western Australia, Crawley, Western Australia 6009, Australia |
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Abstract: | The synthesis of some novel 3′-spirocyclic-oxindole compounds, based on the spiroindole-3,5′-isoxazolidin]-2(1H)-one, the 2′H-spiroindole-3,6′-1,3]oxazinane]-2,2′(1H)-dione and the 2′H-spiroindoline-3,3′-pyrrolo1,2-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. |
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Keywords: | Isoxazolidine Oxazinane Oxindole Nitrones [1 3]-Dipolar cycloaddition Spirocyclic compounds Cytotoxic activity |
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