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

Yong, SR; Ung, AT; Pyne, SG; Skelton, BW; White, AH

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

Yong, SR Ung, AT

Pyne, SG Skelton, BW White, AH

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Publication Type:: Journal Article
Citation:: Tetrahedron, 2007, 63 (25), pp. 5579 - 5586
Issue Date:: 2007-06-18

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Field	Value	Language
dc.contributor.author	Yong, SR	en_US
dc.contributor.author	Ung, AT https://orcid.org/0000-0002-5665-0702	en_US
dc.contributor.author	Pyne, SG	en_US
dc.contributor.author	Skelton, BW	en_US
dc.contributor.author	White, AH	en_US
dc.date.issued	2007-06-18	en_US
dc.identifier.citation	Tetrahedron, 2007, 63 (25), pp. 5579 - 5586	en_US
dc.identifier.issn	0040-4020	en_US
dc.identifier.uri	http://hdl.handle.net/10453/8481
dc.description.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. Crown Copyright © 2007.	en_US
dc.relation.ispartof	Tetrahedron	en_US
dc.relation.isbasedon	10.1016/j.tet.2007.04.028	en_US
dc.subject.classification	Organic Chemistry	en_US
dc.title	Synthesis of novel 3′-spirocyclic-oxindole derivatives and assessment of their cytostatic activities	en_US
dc.type	Journal Article
utslib.citation.volume	25	en_US
utslib.citation.volume	63	en_US
utslib.for	0305 Organic Chemistry	en_US
utslib.for	0304 Medicinal and Biomolecular Chemistry	en_US
pubs.embargo.period	Not known	en_US
pubs.organisational-group	/University of Technology Sydney
pubs.organisational-group	/University of Technology Sydney/Faculty of Science
pubs.organisational-group	/University of Technology Sydney/Faculty of Science/School of Mathematical and Physical Sciences
pubs.organisational-group	/University of Technology Sydney/Strength - CCET - Centre for Clean Energy Technology
utslib.copyright.status	closed_access
pubs.issue	25	en_US
pubs.publication-status	Published	en_US
pubs.volume	63	en_US

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. Crown Copyright © 2007.

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http://hdl.handle.net/10453/8481