Synthesis of Schiff base derivatives of 4-(2-aminoethyl)-benzenesulfonamide with inhibitory activity against carbonic anhydrase isoforms I, II, IX and XII

被引：38

作者：

Durgun, Mustafa ^{[1
]}

Turkmen, Hasan ^{[2
]}

Ceruso, Mariangela ^{[3
]}

Supuran, Claudiu T. ^{[3
,4
]}

机构：

[1] Harran Univ, Fac Arts & Sci, Dept Chem, TR-63190 Sanliurfa, Turkey

[2] Harran Univ, Fac Med, Dept Med Pharmacol, TR-63190 Sanliurfa, Turkey

[3] Univ Florence, Lab Chim Bioinorgan, Polo Sci, I-50019 Florence, Italy

[4] Univ Florence, Neurofarba Dept, Sect Pharmaceut & Nutriceut Sci, I-50019 Florence, Italy

来源：

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS | 2015年 / 25卷 / 11期

关键词：

Carbonic anhydrase; Inhibitor; Sulfonamide; Schiff base; Secondary amine; AROMATIC SULFONAMIDES; COPPER(II) COMPLEXES; THERAPEUTIC APPLICATIONS; METAL-COMPLEXES; ISOZYME-I; ANTIBACTERIAL; PATENT; MECHANISM; SULFANILAMIDE; ANTIFUNGAL;

D O I：

10.1016/j.bmcl.2015.04.007

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

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. (C) 2015 Elsevier Ltd. All rights reserved.

引用

页码：2377 / 2381

页数：5

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