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

Access this Article

Search this Article

Author(s)

Abstract

<p>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 <i>para</i>-position of the phenyl ring. Compounds <b>3b</b>–<b>e</b> showed cytotoxic activity, with IC<sub>50</sub> values ranging from 17–17.44 µM for the cell lines tested, finding the highest effect for compound <b>3e</b>.</p>

Journal

  • Chemical and Pharmaceutical Bulletin

    Chemical and Pharmaceutical Bulletin 65(3), 248-252, 2017

    The Pharmaceutical Society of Japan

Codes

  • NII Article ID (NAID)
    130005397369
  • NII NACSIS-CAT ID (NCID)
    AA00602100
  • Text Lang
    ENG
  • ISSN
    0009-2363
  • NDL Article ID
    028005717
  • NDL Call No.
    Z53-D167
  • Data Source
    NDL  J-STAGE 
Page Top