Synthesis and investigation of inhibition effect of fluorinated sulfonamide derivatives on carbonic anhydrase

Zohra Benfodda (1, 2) , Franck Guillen (3) , Bernard Romestand (4) , Abdelkader Dahmani (1) , Hubert Blancou (1)

1 IBMM - Institut des Biomolécules Max Mousseron [Pôle Chimie Balard]
2 UNIMES - Université de Nîmes
3 S3F Chimie
4 ECOLAG - Ecosystèmes lagunaires : organisation biologique et fonctionnement

Series of perfluoroalkanesulfonamides 1, sodium salt of perfluoroalkanesulfonamides 2 and polyfluoroalkanesulfonamides 3 derivatives were synthesized and characterized by 1H NMR, 13C NMR, 19F NMR, IR and HRMS. Inhibition effects of these compounds on bovine carbonic anhydrase (bCA) and human carbonic anhydrase isoenzyme II (hCA) have been investigated. Comparing IC50 values of the synthesized molecules 1, 2 and 3, it has been found that compound 2b is a more potent inhibitor than acetazolamide on hCA. Moreover 2b does not present cellular toxicity on sheep red globules.

Mots clés: Perfluoroalkanessulfonamides; Sodium salt of perfluoroalkanessulfonamides; carbonic anhydrase; cellular toxicity

Domaines: Chimie organique

Zohra Benfodda, Franck Guillen, Bernard Romestand, Abdelkader Dahmani, Hubert Blancou. Synthesis and investigation of inhibition effect of fluorinated sulfonamide derivatives on carbonic anhydrase. European Journal of Medicinal Chemistry, 2010, 45 (3), pp.1225-1229. ⟨10.1016/j.ejmrech2009.11.052⟩. ⟨hal-00555960⟩