Issue 2, 2018

X-ray crystal structures and anti-breast cancer property of 3-tert-butoxycarbonyl-2-arylthiazolidine-4-carboxylic acids

Abstract

Diastereomeric ‘2RS,4R’-2-arylthiazolidine-4-carboxylic acids (ATCAs) were synthesized and their resolution to chiraly pure N-BOC derivatives was attempted by column chromatography. The absolute stereochemistry of the resolved compounds was ascertained by X-ray single crystal structures. Further application of the synthesized compounds was studied for their in vitro anti-breast cancer activity against MCF7 cell line using DOX as a standard by MTT assay method. Cell morphology analysis was carried out by fluorescence microscopy. The compounds containing ‘2S’ absolute configuration in thiazolidine ring and presence of 2-NO2, 2,6-Cl groups on ‘2R’-aryl substituent showed significant anti-breast cancer activity where some of the compounds were found to be more active than DOX in terms of induced apoptosis mode of MCF7 cell death.

Graphical abstract: X-ray crystal structures and anti-breast cancer property of 3-tert-butoxycarbonyl-2-arylthiazolidine-4-carboxylic acids

Supplementary files

Article information

Article type
Paper
Submitted
09 Aug 2017
Accepted
05 Dec 2017
First published
05 Dec 2017

New J. Chem., 2018,42, 1078-1086

X-ray crystal structures and anti-breast cancer property of 3-tert-butoxycarbonyl-2-arylthiazolidine-4-carboxylic acids

R. M. Jagtap, S. H. Thorat, R. G. Gonnade, A. A. Khan and S. K. Pardeshi, New J. Chem., 2018, 42, 1078 DOI: 10.1039/C7NJ02961F

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