期刊
MOLECULAR DIVERSITY
卷 19, 期 2, 页码 251-261出版社
SPRINGER
DOI: 10.1007/s11030-015-9574-6
关键词
Withaferin-A; Spiro-pyrrolizidino oxindole/acenaphthoquinone; Azomethine ylide cycloaddition; 1D/2D NMR; X-ray crystallography
类别
资金
- Council of Scientific and Industrial Research Government of India
- CSIR
Withaferin-A (WA) has attracted the attention of chemists as well as biologists due to its interesting structure and various bio-activities. In light of the promising biological importance of WA as well as pyrrolidine-2-spiro-3-oxindole ring system, we became interested in the synthesis of a combined motif involving both the ring systems via the 1,3-dipolar cycloaddition of WA at -bond of the ,-unsaturated carbonyl system. We now report a facile, atom-economic synthesis of novel spiro-pyrrolizidino-oxindole adducts of withaferin-A (10 compounds) via the intermolecular cycloaddition of azomethine ylides generated in situ from proline and isatins/acenaphthoquinone. The reaction is highly chemo, regio, and stereoselective affording the cis-fused products with -orienting hydrogen. The structures were determined by 1D/2D NMR spectroscopic data analysis and unequivocally confirmed by X-ray crystallographic analysis in some cases. Bioevaluation of the compounds against six cancer lines (e.g., CHO, HepG2, HeLa, HEK 293, MDCK-II, and Caco-2) identified 4 promising potential anticancer compounds.
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