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INVESTIGATION ON THE SYNTHESIS OF NEW 3-[4-(ARYLALKOXY)PHENYLETHYL]-2-THIOXO-1,3-THIAZOLIDIN-4-ONES AND THEIR BIOLOGICAL EVALUATION AGAINST CANCER CELLS

Camille D. Dago, Christelle N'ta Ambeu, Wacothon K. Coulibaly, Janat A. Mamyrbekova-Bekro, Rémy Le Guével, Anne Corlu, Jean-Pierre Bazureau
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Abstract


Herein, we report on the 5-step synthesis of new 3-[4-(arylalkoxy)phenylethyl]-2-thioxo-1,3-thiazolidin-4-ones without 5-arylidene fragments starting from tyramine The construction involved protection with Boc2O, regioselective O-alkylation, deprotection with 6 M HCl, neutralization, and finally reaction of bis(carboxymethyl)trithiocarbonate under microwave irradiation. The intermediates and the N-substituted rhodanine have been also evaluated for their in vitro inhibition of cell proliferation (Huh7, Caco 2, MDA-MB231, HCT 116, PC3, NCI-H727, HaCat). Two compounds have shown a selective potent activity against HCT116 cell line.

Keywords


3-[4-(arylalkoxy)phenylethyl]-2-thioxo-1,3-thiazolidin-4-one; rhodanine; microwave irradiation; tumoral cell lines

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