An efficient strategy for the synthesis of 1-(trifluoromethylsulfonamido)-propan-2-yl esters and the evaluation of their cytotoxic activity

Omar Gómez-García, Elizabeth Gómez, César Monzón-González, Teresa Ramírez-Apan, Cecilio Álvarez-Toledano

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1 Scopus citations

Abstract

© 2017 The Pharmaceutical Society of Japan. An efficient method for the synthesis of 1-(trifluoromethylsulfonamido)propan-2-yl benzoates is described, the products of the reaction were characterized by heteronuclear single quantum coherence spectroscopy (HSQC), heteronuclear multiple bond correlation (HMBC) and NMR experiments. The overall process began with the activation of the oxazoline ring by triflic anhydride, followed by the opening of the five-membered ring in the 5-methyl-2-phenyl-4,5-dihydrooxazole system. The cytotoxic activity of the new trifluoromethyl sulfonamides was evaluated with six cancer cell lines and human gingival fibroblasts, posteriorly analyzing the influence on cytotoxicity exerted by the withdrawing and donor substituents at the para-position of the phenyl ring. Compounds 3b-e showed cytotoxic activity, with IC50values ranging from 17-17.44 μM for the cell lines tested, finding the highest effect for compound 3e.
Original languageAmerican English
Pages (from-to)248-252
Number of pages5
JournalChemical and Pharmaceutical Bulletin
DOIs
StatePublished - 1 Jan 2017

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