TY - JOUR
T1 - An efficient strategy for the synthesis of 1-(trifluoromethylsulfonamido)-propan-2-yl esters and the evaluation of their cytotoxic activity
AU - Gómez-García, Omar
AU - Gómez, Elizabeth
AU - Monzón-González, César
AU - Ramírez-Apan, Teresa
AU - Álvarez-Toledano, Cecilio
N1 - Publisher Copyright:
© 2017 The Pharmaceutical Society of Japan.
PY - 2017
Y1 - 2017
N2 - 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 17-17.44 μM for the cell lines tested, finding the highest effect for compound 3e.
AB - 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 17-17.44 μM for the cell lines tested, finding the highest effect for compound 3e.
KW - Cytotoxic activity
KW - NMR
KW - Oxazoline
KW - Ring opening reaction
KW - Sulfonamide
UR - http://www.scopus.com/inward/record.url?scp=85014588871&partnerID=8YFLogxK
U2 - 10.1248/cpb.c16-00724
DO - 10.1248/cpb.c16-00724
M3 - Artículo
C2 - 28250346
SN - 0009-2363
VL - 65
SP - 248
EP - 252
JO - Chemical and Pharmaceutical Bulletin
JF - Chemical and Pharmaceutical Bulletin
IS - 3
ER -