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Synthesis of some N-aroyl-2-oxindole benzenesulfonamide conjugates with carbonic anhydrase inhibitory activity.

Abstract：

:Implication of carbonic anhydrases (CAs) in many physiological functions made them attractive therapeutic targets. Herein, we report the synthesis of three series of benzenesulfonamide-based compounds (5a-e, 9a-e and 10a-e) as potential ligands to four of the human CA isoforms (hCA I, hCA II, hCA IX and hCA XII). All synthesized compounds were evaluated for their CA inhibitory activity. Most of the compounds preferentially inhibited the tumor-associated isoforms IX and XII. Series 9a-e and 10a-e showed the highest activity. Of particular interest was compound 10a which demonstrated the highest activity among all compounds with Ki of 68.3 and 21.5 nM against hCA IX and hCA XII, respectively, in addition to its highest selectivity index. To get deep insight on the interaction of compound 10a with CA, docking experiment was run to study the binding interaction with key amino acids and zinc ion in the catalytic site of the four isoforms studied.

journal_name

Bioorg Chem

journal_title

Bioorganic chemistry

authors

George RF,Bua S,Supuran CT,Awadallah FM

doi

10.1016/j.bioorg.2020.103635

subject

Has Abstract

pub_date

2020-03-01 00:00:00

pages

103635

eissn

0045-2068

issn

1090-2120

pii

S0045-2068(19)32045-0

journal_volume

96

pub_type

杂志文章

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