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Synthesis and DFT studies of an antitumor active spiro-oxindole
Stockholm University, Faculty of Science, Department of Organic Chemistry.
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Number of Authors: 8
2015 (English)In: New Journal of Chemistry, ISSN 1144-0546, E-ISSN 1369-9261, Vol. 39, no 10, 8017-8027 p.Article in journal (Refereed) Published
Abstract [en]

An anti-oncological active spiro-oxindole 7 was synthesized regioselectively via a [3+2]-cycloaddition reaction of azomethine ylide to exocyclic olefinic linkage of 4-piperidone 6, exhibiting properties against diverse tumor cell lines including leukemia, melanoma and cancers of the lung, colon, brain, ovary, breast, prostate, and kidney. Compound 7 crystallizes in the monoclinic system and P21/c space group with four molecules in the unit cell. The structure was also studied by AM1, PM3 and DFT techniques. DFT studies support the stereochemical selectivity of the reaction and determine the molecular electrostatic potential and frontier molecular orbitals.

Place, publisher, year, edition, pages
2015. Vol. 39, no 10, 8017-8027 p.
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Organic Chemistry
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URN: urn:nbn:se:su:diva-123211DOI: 10.1039/c5nj01109dISI: 000362355200068OAI: oai:DiVA.org:su-123211DiVA: diva2:872210
Available from: 2015-11-18 Created: 2015-11-18 Last updated: 2015-11-18Bibliographically approved

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Stawinski, Jacek
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