4-Sulfamoylphenylalkylamides as Inhibitors of Carbonic Anhydrases Expressed in Vibrio cholerae

被引:5
|
作者
Mancuso, Francesca [1 ]
De Luca, Laura [1 ]
Bucolo, Federica [1 ]
Vrabel, Milan [2 ]
Angeli, Andrea [3 ]
Capasso, Clemente [4 ]
Supuran, Claudiu T. [3 ]
Gitto, Rosaria [1 ]
机构
[1] Univ Messina, CHIBIOFARAM Dept, Viale Stagno DAlcontres, I-98166 Messina, Italy
[2] Czech Acad Sci, Inst Organ Chem & Biochem IOCB, Flemingovo Nam 2, Prague 16000, Czech Republic
[3] Univ Florence, NEUROFARBA Dept, Via U Schiff 6, I-50019 Florence, Italy
[4] CNR, Inst Biosci & Bioresources, Via Castellino 111, I-80131 Naples, Italy
关键词
Drug Discovery; Sulfonamides; Enzymes Inhibitors; Vibrio cholerae; Bacterial carbonic anhydrases; ALPHA; BACTERIAL; PROFILES; DISCOVERY;
D O I
10.1002/cmdc.202100510
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
A current issue of antimicrobial therapy is the resistance to treatment with worldwide consequences. Thus, the identification of innovative targets is an intriguing challenge in the drug and development process aimed at newer antimicrobial agents. The state-of-art of anticholera therapy might comprise the reduction of the expression of cholera toxin, which could be reached through the inhibition of carbonic anhydrases expressed in Vibrio cholerae (VchCA alpha, VchCA beta, and VchCA gamma). Therefore, we focused our interest on the exploitation of sulfonamides as VchCA inhibitors. We planned to design and synthesize new benzenesulfonamides based on our knowledge of the VchCA catalytic site. The synthesized compounds were tested thus collecting useful SAR information. From our investigation, we identified new potent VchCA inhibitors, some of them displayed high affinity toward VchCA gamma class, for which few inhibitors are currently reported in literature. The best interesting VchCA gamma inhibitor (S)-N-(1-oxo-1-((4-sulfamoylbenzyl)amino)propan-2-yl)furan-2-carboxamide (40) resulted more active and selective inhibitor when compared with acetazolamide (AAZ) as well as previously reported VchCA inhibitors.
引用
收藏
页码:3787 / 3794
页数:8
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