Facile synthesis and quantitative structure-activity relationship study of antitumor active 2-(4-Oxo-thiazolidin-2-ylidene)-3-oxo-propionitriles

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Abstract

2-(5-Arylidene-4-oxo-3-phenyl-thiazolidin-2-ylidene)-3-oxo-propionitriles 4a-j were prepared via condensation of aromatic aldehydes with 4-thiazolidinones 3a, b. The latter was obtained via electrophilic attack of phenylisothiocyanate on 3-oxo-propionitriles 1a, b followed by reaction with chloroacetyl chloride under basic condition. Additionally, 2-(5-heteroalicyclic methylene) analogues 5a-h were prepared via Mannich reaction of the appropriate secondary amines and formaldehyde with 4-thiazolidinones 3a, b. Many of the synthesized compounds exhibited promising antitumor properties against colon HCT116 and breast T47D cell lines. 3D-Pharmacophore modeling and quantitative structure-activity relationship (QSAR) analysis were combined to explain the observed antitumor properties. © 2012 The Pharmaceutical Society of Japan.

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Hanna, M. M., & George, R. F. (2012). Facile synthesis and quantitative structure-activity relationship study of antitumor active 2-(4-Oxo-thiazolidin-2-ylidene)-3-oxo-propionitriles. Chemical and Pharmaceutical Bulletin, 60(9), 1195–1206. https://doi.org/10.1248/cpb.c12-00498

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