Discovery of 1,1′-Biphenyl-4-sulfonamides as a New Class of Potent and Selective Carbonic Anhydrase XIV Inhibitors

被引：35

作者：

La Regina, Giuseppe ^{[1
]}

Coluccia, Antonio ^{[1
]}

Famiglini, Valeria ^{[1
]}

Pelliccia, Sveva ^{[1
]}

Monti, Ludovica ^{[1
]}

Vullo, Daniela ^{[2
]}

Nuto, Elisa ^{[3
]}

Aterio, Vincenzo ^{[4
]}

De Simone, Giuseppina ^{[4
]}

Monti, Simona Maria ^{[4
]}

Pan, Peiwen ^{[5
,6
]}

Parkkila, Seppo ^{[5
,6
]}

Supuran, Claudiu T. ^{[2
]}

Rossello, Armando ^{[3
]}

Silvestri, Romano ^{[1
]}

机构：

[1] Univ Roma La Sapienza, Ist Pasteur Italia, Fdn Cenci Bolognetti, Dipartimento Chim & Tecnol Farmaco, Piazzale Aldo Moro 5, I-00185 Rome, Italy

[2] Univ Florence, Dipartimento Neurofarba, Sez Sci Farmaceut & Nutraceut, I-50019 Florence, Italy

[3] Univ Pisa, Dipartimento Farm, I-56126 Pisa, Italy

[4] CNR, Ist Biostrutture & Bioimmmagini, I-80134 Naples, Italy

[5] Univ Tampere, Sch Med, Tampere 33014, Finland

[6] Tampere Univ Hosp, Tampere 33014, Finland

来源：

JOURNAL OF MEDICINAL CHEMISTRY | 2015年 / 58卷 / 21期

关键词：

DRUG DESIGN; CRYSTALLOGRAPHY; TARGETS; IX;

D O I：

10.1021/acs.jmedchem.5b01144

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

New 1,1'-biphenylsulfonamides were synthesized and evaluated as inhibitors of the ubiquitous human carbonic anhydrase isoforms I, II, IX, XII, and XIV using acetazolamide (AAZ) as reference compound. The sulfonamides 1-21 inhibited all the isoforms, with K-i values in the nanomolar range of concentration, and were superior to AAZ against all of them. X-ray crystallography and molecular modeling studies on the adducts that compound 20, the most potent hCA XIV inhibitor of the series (K-i, = 0.26 nM), formed with the five hCAs, provided insight into the molecular determinants responsible for the high affinity of this molecule toward the target enzymes. The results pave the way to the development of 1.1'-biphenylsulfonamides as a new class of highy potent hCA XIV inhibitors.

引用

页码：8564 / 8572

页数：9

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