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Sulfonamides incorporating piperazine bioisosteres as potent human carbonic anhydrase I, II, IV and IX inhibitors.

Abstract：

:Starting from the molecular simplification of (R) 4-(3,4-dibenzylpiperazine-1-carbonyl)benzenesulfonamide 9a, a compound endowed with selectivity for human Carbonic Anhydrase (hCA) IV, a series of piperazines and 4-aminopiperidines carrying a 4-sulfamoylbenzamide moiety as Zn-binding group have been designed and tested on human isoforms hCA I, II, IV and IX, using a stopped flow CO2 hydrase assay. The aim of the work was to derive structure-activity relationships useful for designing isoform selective compounds. These structural modifications changed the selectivity profile of the analogues from hCA IV to hCA I and II, and improved potency. Several of the new compounds showed subnanomolar activity on hCA II. X-ray crystallography of ligand-hCAII complexes was used to compare the binding modes of the new piperazines and the previously synthesized 2-benzyl-piperazine analogues, explaining the inhibition profiles.

journal_name

Bioorg Chem

journal_title

Bioorganic chemistry

authors

Chiaramonte N,Bua S,Angeli A,Ferraroni M,Picchioni I,Bartolucci G,Braconi L,Dei S,Teodori E,Supuran CT,Romanelli MN

doi

10.1016/j.bioorg.2019.103130

subject

Has Abstract

pub_date

2019-10-01 00:00:00

pages

103130

eissn

0045-2068

issn

1090-2120

pii

S0045-2068(19)30931-9

journal_volume

91

pub_type

杂志文章

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