Synthesis of Schiff base derivatives of 4-(2-aminoethyl)-benzenesulfonamide with inhibitory activity against carbonic anhydrase isoforms I, II, IX and XII.
Schiff base derivatives were obtained by reaction of 4-(2-aminoethyl)benzenesulfonamide with aromatic aldehydes. The corresponding secondary amine derivatives were also prepared by reduction of the imine compounds with NaBH4. These derivatives were investigated as inhibitors of four human carbonic anhydrase (CA, EC 4.2.1.1) isoforms, the cytosolic isozymes hCA I and II, as well as, the transmembrane, tumor-associated hCA IX and XII. Some of the newly synthesised compounds showed effective inhibitory activities against these CA isozymes. Many low nanomolar inhibitors were detected against all isoforms among the secondary amines whereas the Schiff bases were by far less active compared to the corresponding reduced derivatives among all investigated isoforms.
Department of Chemistry, Faculty of Arts and Sciences, Harran University, 63190 Sanliurfa, Turkey. Electronic address: mustafadurgun@harran.edu.tr.
Mustafa
M
Durgun
Department of Medical Pharmacology, Faculty of Medicine, Harran University, 63190 Sanliurfa, Turkey.
Hasan
H
Turkmen
Università degli Studi di Firenze, Polo Scientifico, Laboratorio di Chimica Bioinorganica, Rm. 188, Via della Lastruccia 3, 50019 Sesto Fiorentino (Florence), Italy.
Mariangela
M
Ceruso
Università degli Studi di Firenze, Polo Scientifico, Laboratorio di Chimica Bioinorganica, Rm. 188, Via della Lastruccia 3, 50019 Sesto Fiorentino (Florence), Italy; Università degli Studi di Firenze, Neurofarba Dept., Section of Pharmaceutical and Nutriceutical Sciences, Via U. Schiff 6, 50019 Sesto Fiorentino (Florence), Italy. Electronic address: claudiu.supuran@unifi.it.
Claudiu T
CT
Supuran
D002257:Carbonic Anhydrase Inhibitors / Q000737:chemistry* / Q000494:pharmacology*; D002256:Carbonic Anhydrases / Q000145:classification*; D007097:Imines / Q000737:chemistry / Q000494:pharmacology; D007527:Isoenzymes / Q000037:antagonists & inhibitors; D015394:Molecular Structure; D013449:Sulfonamides / Q000737:chemistry*
D002257:Carbonic Anhydrase Inhibitors; D007097:Imines; D007527:Isoenzymes; D013449:Sulfonamides; D002256:Carbonic Anhydrases
Carbonic anhydrase; Inhibitor; Schiff base; Secondary amine; Sulfonamide