title: An Efficient Strategy for the Synthesis of 1-(Trifluoromethylsulfonamido)propan-2-yl Esters and the Evaluation of Their Cytotoxic Activity.
abstract: 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.
authors.affiliation: Departamento Química Orgánica, Escuela Nacional de Ciencias Biológicas-IPN, Prolongación de Carpio y Plan de Ayala S/N.
authors.forename: Omar
authors.initials: O
authors.lastname: Gómez-García
authors.forename: Elizabeth
authors.initials: E
authors.lastname: Gómez
authors.forename: César
authors.initials: C
authors.lastname: Monzón-González
authors.forename: Teresa
authors.initials: T
authors.lastname: Ramírez-Apan
authors.forename: Cecilio
authors.initials: C
authors.lastname: Álvarez-Toledano
mesh_terms: D045744:Cell Line, Tumor; D002470:Cell Survival / Q000187:drug effects; D004305:Dose-Response Relationship, Drug; D004952:Esters / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology / Q000633:toxicity; D005347:Fibroblasts / Q000187:drug effects; D005881:Gingiva / Q000166:cytology; D006801:Humans; D015394:Molecular Structure; D013329:Structure-Activity Relationship; D013449:Sulfonamides / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology* / Q000633:toxicity*
chemical_list: D004952:Esters; D013449:Sulfonamides