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Development of sulfonamides incorporating phenylacrylamido functionalities as carbonic anhydrase isoforms I, II, IX and XII inhibitors.

Abstract：

:A series of novel sulfonamides incorporating phenylacrylamido functionalities were synthesized and investigated for the inhibition of the metalloenzyme carbonic anhydrase (CA, EC 4.2.1.1). The physiologically and pharmacologically relevant human (h) isoforms hCA I and II (cytosolic isozymes), as well as the transmembrane tumor-associated hCA IX and XII were included in the study. These compounds showed low nanomolar or sub-nanomolar inhibition constants against hCA II (KIs in the range of 0.50-50.5nM), hCA IX (KIs of 1.8-228.5nM), and hCA XII (KIs of 3.5-96.2nM) being less effective as inhibitors of the off target isoform hCA I. A detailed structure-activity relationship study demonstrates that the nature and position of substituents present on the aromatic part of the scaffold strongly influence the inhibition of CA isoforms. As hCA II, IX and XII are involved in pathologies such as glaucoma and hypoxic, and metastatic tumors, compounds of the type reported in this work may be useful preclinical candidates.

journal_name

Bioorg Med Chem

journal_title

Bioorganic & medicinal chemistry

authors

Angapelly S,Ramya PVS,Angeli A,Del Prete S,Capasso C,Arifuddin M,Supuran CT

doi

10.1016/j.bmc.2017.08.047

subject

Has Abstract

pub_date

2017-10-15 00:00:00

pages

5726-5732

issue

20

eissn

0968-0896

issn

1464-3391

pii

S0968-0896(17)31520-1

journal_volume

25

pub_type

杂志文章

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