An Efficient Strategy for the Synthesis of 1-(Trifluoromethylsulfonamido)-propan-2-yl Esters and the Evaluation of Their Cytotoxic Activity

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 IC50 values ranging from 17-17. 44μM for the cell lines tested, finding the highest effect for compound 3e.