Phosphorus versus Sulfur: Discovery of Benzenephosphonamidates as Versatile Sulfonamide-Mimic Chemotypes Acting as Carbonic Anhydrase Inhibitors

被引：47

作者：

Nocentini, Alessio ^{[1
,2
]}

Gratteri, Paola ^{[1
]}

Supuran, Claudiu T. ^{[2
]}

机构：

[1] Univ Firenze, Dept NEUROFARBA, Pharmaceut & Nutraceut Sect, Lab Mol Modeling Cheminformat & QSAR, Via Ugo Schiff 6, I-50019 Sesto Fiorentino, Italy

[2] Univ Firenze, Dept NEUROFARBA, Pharmaceut & Nutraceut Sect, Via Ugo Schiff 6, I-50019 Sesto Fiorentino, Italy

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2019年 / 25卷 / 05期

关键词：

carbonic anhydrase; inhibition; metallo-enzymes; MM-GBSA; phosphonamidate; QPLD; zinc-binder; ZINC-BINDING GROUP; PHOSPHONAMIDATE; IX;

D O I：

10.1002/chem.201805039

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The first zinc-binding group (ZBG) to have been identified as inhibitor of the metallo-enzymes carbonic anhydrases (CA, EC 4.2.1.1) was the sulfonamide. From then on several classes of zinc-binders have been described. This work reports the benzenephosponamidates as a new chiral aromatic sulfonamide-mimic ZBG able to meet the requirements for effectively binding the enzyme active site. Several low micromolar CA I, II, VII, IX inhibitors were thus detected. Kinetic studies, QM-polarized ligand docking, and MM-GBSA in silico methods were used to characterize this newly identified CA inhibitor chemotype.

引用

页码：1188 / 1192

页数：5

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