Sulfonamides incorporating heteropolycyclic scaffolds show potent inhibitory action against carbonic anhydrase isoforms I, II, IX and XII

被引：20

作者：

Barresi, Elisabetta ^{[1
]}

Salerno, Silvia ^{[1
]}

Marini, Anna Maria ^{[1
]}

Taliani, Sabrina ^{[1
]}

La Motta, Concettina ^{[1
]}

Simorini, Francesca ^{[1
]}

Da Settimo, Federico ^{[1
]}

Vullo, Daniela ^{[2
]}

Supuran, Claudiu T. ^{[3
]}

机构：

[1] Univ Pisa, Dipartimento Farm, Via Bonanno 6, I-56126 Pisa, Italy

[2] Univ Florence, Polo Sci, Lab Chim Bioinorgan, Rm 188,Via Lastruccia 3, I-50019 Florence, Italy

[3] Univ Florence, NEUROFARBA Dept, Sez Sci Farmaceut & Nutraceut, Via Ugo Schiff 6, I-50019 Florence, Italy

来源：

BIOORGANIC & MEDICINAL CHEMISTRY | 2016年 / 24卷 / 04期

关键词：

Carbonic anhydrase; Sulfonamide; Carboxylic acid; Benzothiopyranopyrimidine; Pyridothiopyranopyrimidine; Dihydrbenzothiopyrano[4,3-c]pyrazole; LOWERING AROMATIC/HETEROCYCLIC SULFONAMIDES; ISOZYME-II; BIOCHEMICAL-CHARACTERIZATION; MYCOBACTERIUM-TUBERCULOSIS; SELECTIVE INHIBITORS; PHENOLIC-COMPOUNDS; LIGAND-BINDING; MOIETIES; AGENTS; RING;

D O I：

10.1016/j.bmc.2016.01.018

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

Three series of polycyclic compounds possessing either primary sulfonamide or carboxylic acid moieties as zinc-binding groups were investigated as inhibitors of four physiologically relevant CA isoforms, the cytosolic hCA I and II, as well as the transmembrane hCA IX and XII. Most of the new sulfonamides reported here showed excellent inhibitory effects against isoforms hCA II, IX and XII, but no highly isoform-selective inhibition profiles. On the other hand, the carboxylates selectively inhibited hCA IX (K(I)s ranging between 40.8 and 92.7 nM) without inhibiting significantly the other isoforms. Sulfonamides/carboxylates incorporating polycyclic ring systems such as benzothiopyranopyrimidine, pyridothiopyranopyrimidine or dihydrobenzothiopyrano[4,3-c] pyrazole may be considered as interesting candidates for exploring the design of isoform-selective CAIs with various pharmacologic applications. (C) 2016 Elsevier Ltd. All rights reserved.

引用

页码：921 / 927

页数：7

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