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New Dihydrothiazole Benzensulfonamides: Looking for Selectivity toward Carbonic Anhydrase Isoforms I, II, IX, and XII.

ABSTRACT: In the present study we investigated the structure-activity relationships of a new series of 4-[(3-ethyl-4-aryl-2,3-dihydro-1,3-thiazol-2-ylidene)amino]benzene-1-sulfonamides (EMAC10101a-m). All synthesized compounds, with the exception of compound EMAC10101k, preferentially inhibit off-target hCA II isoform. Within the series, compound EMAC10101d, bearing a 2,4-dichorophenyl substituent in position 4 of the dihydrothiazole ring, was the most potent and selective toward hCA II with an inhibitory activity in the low nanomolar range.

SUBMITTER: Meleddu R

PROVIDER: S-EPMC7236253 | biostudies-literature | 2020 May

REPOSITORIES: biostudies-literature

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New Dihydrothiazole Benzensulfonamides: Looking for Selectivity toward Carbonic Anhydrase Isoforms I, II, IX, and XII.

Meleddu Rita R Distinto Simona S Cottiglia Filippo F Angius Rossella R Caboni Pierluigi P Angeli Andrea A Melis Claudia C Deplano Serenella S Alcaro Stefano S Ortuso Francesco F Supuran Claudiu T CT Maccioni Elias E

ACS medicinal chemistry letters 20200213 5

In the present study we investigated the structure-activity relationships of a new series of 4-[(3-ethyl-4-aryl-2,3-dihydro-1,3-thiazol-2-ylidene)amino]benzene-1-sulfonamides (EMAC10101a-m). All synthesized compounds, with the exception of compound EMAC10101k, preferentially inhibit off-target hCA II isoform. Within the series, compound EMAC10101d, bearing a 2,4-dichorophenyl substituent in position 4 of the dihydrothiazole ring, was the most potent and selective towa ...[more]

PMID: 32435395

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Targeting carbonic anhydrase IX and XII isoforms with small molecule inhibitors and monoclonal antibodies.

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