Carbonic anhydrase inhibitors: Synthesis, molecular docking, cytotoxic and inhibition of the human carbonic anhydrase isoforms I, II, IX, XII with novel benzenesulfonamides incorporating pyrrole, pyrrolopyrimidine and fused pyrrolopyrimidine moieties

被引：61

作者：

Ghorab, Mostafa M. ^{[1
,2
]}

Alsaid, Mansour S. ^{[1
]}

Ceruso, Mariangela ^{[3
]}

Nissan, Yassin M. ^{[4
]}

Supuran, Claudiu T. ^{[3
,5
,6
]}

机构：

[1] King Saud Univ, Coll Pharm, Dept Pharmacognosy, Riyadh 11451, Saudi Arabia

[2] Atom Energy Author, Natl Ctr Radiat Res & Technol, Drug Radiat Res Dept, Cairo, Egypt

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

[4] Cairo Univ, Fac Pharm, Dept Pharmaceut Chem, Cairo, Egypt

[5] Univ Florence, Dipartimento Neurofaba, I-50019 Florence, Italy

[6] Sez Sci Farmaceut & Nutraceut, I-50019 Florence, Italy

来源：

BIOORGANIC & MEDICINAL CHEMISTRY | 2014年 / 22卷 / 14期

关键词：

Pyrrolopyrimidines; Sulfonamide; Cytotoxic activity; Carbonic anhydrase inhibitors; Molecular docking; PYRIMIDINE-DERIVATIVES; BIOLOGICAL EVALUATION; ANTICANCER; SULFONAMIDES; AGENTS; ANTIBACTERIAL; ACTIVATORS; COUMARINS; MECHANISM; BEARING;

D O I：

10.1016/j.bmc.2014.05.009

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 novel pyrroles, pyrrolopyrimidines, pyrazolopyrrolopyrimidine, triazolopyrrolopyrimidines, tetrazolopyrrolopyrimidine, triazinopyrrolopyrimidines and pyrrolopyrimidotriazepines bearing the biologically active benzenesulfonamide moiety were synthesized by using pyrrole-o-amino-carbonitrile as key intermediate. All the synthesized compounds were evaluated for their in vitro carbonic anhydrase (CA, EC 4.2.1.1) inhibitory effects against the human (h) isoforms hCA I, II, IX and XII. Among the tested derivatives, compounds 16, 18 and 20-24 showed potent activity as inhibitors for the tumor associated transmembrane isoforms (hCA IX and XII) in the nanomolar and subnanomolar range, with high selectivity. All compounds underwent cytotoxic activity assays on human breast cancer cell line (MCF-7) showing effective activity, comparable to that of the clinically used drug doxorubicin. (C) 2014 Elsevier Ltd. All rights reserved.

引用

页码：3684 / 3695

页数：12

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