Synthesis, biological evaluation and computational studies of novel iminothiazolidinone benzenesulfonamides as potent carbonic anhydrase II and IX inhibitors

被引：28
|
作者：
Mahmood, Shams-ul [1 ]
Saeed, Aamer [1 ]
Bua, Sivia [2 ]
Nocentini, Alessio [2 ,3 ,4 ]
Gratteri, Paola [3 ,4 ]
Supuran, Claudiu T. [2 ]
机构：
[1] Quaid I Azam Univ, Dept Chem, Islamabad 45320, Pakistan
[2] Univ Florence, Dept NEUROFARBA, Pharmaceut & Nutraceut Sect, Via Ugo Schiff 6, I-50019 Florence, Italy
[3] Univ Florence, Dept NEUROFARBA, Sect Pharmaceut & Nutraceut Sci, Lab Mol Modeling Cheminformat,Pole Sci, Via U Schiff 6, I-50019 Florence, Italy
[4] Univ Florence, QSAR, Polo Sci, Via U Schiff 6, I-50019 Florence, Italy
来源：
BIOORGANIC CHEMISTRY | 2018年 / 77卷
关键词：
Carbonic anhydrase; Zinc-binding group; Nanomolar inhibition; Anti-glaucoma; Anti-tumour; ANTICANCER AGENTS; DESIGN; SULFONAMIDES; MOIETIES; DRUG; DERIVATIVES; ACTIVATORS; DISCOVERY; CANCER; BASES;
D O I：
10.1016/j.bioorg.2018.01.031
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：
A series of iminothiazolidinone-sulfonamide hybrids (2a-k) was synthesized by heterocyclization of sulfanilamide thioureas with methyl bromoacetate and characterized by spectroscopic techniques, mass and elemental analysis. The synthesized derivatives were screened against four relevant human (h) isoforms of carbonic anydrases (CAs, EC 4.2.1.1) I, II, IV and IX. These enzymes are involved in a variety of diseases, including glaucoma, retinitis pigmentosa, epilepsy, arthritis, and tumors. Derivatives 2a-2k exhibited the best inhibitory activity against the cytosolyc hCA II (Kis are reaching the sub-nanomolar range, 0.41-37.8 nM) and against the tumor-associated isoform hCA IX (Kis are spanning between 24.3 and 368.3 nM). The binding mode of the reported iminothiazolidinone benzenesulfonamides within hCA II and IX catalytic clefts was investigated by docking studies. (C) 2018 Elsevier Inc. All rights reserved.
引用
收藏
页码：381 / 386
页数：6
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