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Tetrahydroquinazole-based secondary sulphonamides as carbonic anhydrase inhibitors: synthesis, biological evaluation against isoforms I, II, IV, and IX, and computational studies.

ABSTRACT: A library of variously decorated N-phenyl secondary sulphonamides featuring the bicyclic tetrahydroquinazole scaffold was synthesised and biologically evaluated for their inhibitory activity against human carbonic anhydrase (hCA) I, II, IV, and IX. Of note, several compounds were identified showing submicromolar potency and excellent selectivity for the tumour-related hCA IX isoform. Structure-activity relationship data attained for various substitutions were rationalised by molecular modelling studies in terms of both inhibitory activity and selectivity.

SUBMITTER: Baglini E

PROVIDER: S-EPMC8344263 | biostudies-literature | 2021 Dec

REPOSITORIES: biostudies-literature

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Tetrahydroquinazole-based secondary sulphonamides as carbonic anhydrase inhibitors: synthesis, biological evaluation against isoforms I, II, IV, and IX, and computational studies.

Baglini Emma E Ravichandran Rahul R Berrino Emanuela E Salerno Silvia S Barresi Elisabetta E Marini Anna Maria AM Viviano Monica M Castellano Sabrina S Da Settimo Federico F Supuran Claudiu T CT Cosconati Sandro S Taliani Sabrina S

Journal of enzyme inhibition and medicinal chemistry 20211201 1

A library of variously decorated <i>N</i>-phenyl secondary sulphonamides featuring the bicyclic tetrahydroquinazole scaffold was synthesised and biologically evaluated for their inhibitory activity against human carbonic anhydrase (hCA) I, II, IV, and IX. Of note, several compounds were identified showing submicromolar potency and excellent selectivity for the tumour-related hCA IX isoform. Structure-activity relationship data attained for various substitutions were rationalised by molecular mod ...[more]

PMID: 34340614

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