Synthesis and DFT studies of an antitumor active spiro-oxindole
Document Type
Article
Publication Title
New Journal of Chemistry
Abstract
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.
First Page
8017
Last Page
8027
DOI
10.1039/c5nj01109d
Publication Date
7-30-2015
Recommended Citation
Girgis, Adel S.; Mabied, Ahmed F.; Stawinski, Jacek; Hegazy, Lamees; George, Riham F.; Farag, Hanaa; Shalaby, El Sayed M.; and Farag, I. S.Ahmed, "Synthesis and DFT studies of an antitumor active spiro-oxindole" (2015). Pharmaceutical and Administrative Sciences Faculty Publications. 97.
https://doi.org/10.1039/c5nj01109d
https://collections.uhsp.edu/pharm-admin-sciences_pubs/97