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2023•Mendeleev CommunicationsRequires access

A new way of synthesizing heterocyclic primary sulfonamide probes for carbonic anhydrase

Vasilisa Krivovicheva, Andrey Bubyrev, Stanislav Kalinin, Dmitry Dar’in, Maxim Gureev, Daniela Vullo, Mikhail Krasavin, М. К. Корсаков, Claudiu T. Supuran

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Abstract

An N , N -bis( p -methoxybenzyl)-protected α-acetyl-α-diazo-methane sulfonamide proved to be a useful building block for accessing new 5-methyl-1,2,3-thiadiazole-4-sulfonamide as well as methyl 3-sulfamoyl-1 H -pyrazole-5-carboxylate. The latter was further subjected to N -alkylation and N -arylation reactions. All resulting compounds showed potent inhibition of I, II and particularly of cancer-related IX and XII isoforms of human carbonic anhydrase.

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What this paper is about

An N , N -bis( p -methoxybenzyl)-protected α-acetyl-α-diazo-methane sulfonamide proved to be a useful building block for accessing new 5-methyl-1,2,3-thiadiazole-4-sulfonamide as well as methyl 3-sulfamoyl-1 H -pyrazole-5-carboxylate. The latter was further subjected to N -alkylation and N -arylation reactions. All resulting compounds showed potent inhibition of I, II and particularly of cancer-related IX and XII isoforms of human carbonic anhydrase.

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Available abstract

An N , N -bis( p -methoxybenzyl)-protected α-acetyl-α-diazo-methane sulfonamide proved to be a useful building block for accessing new 5-methyl-1,2,3-thiadiazole-4-sulfonamide as well as methyl 3-sulfamoyl-1 H -pyrazole-5-carboxylate. The latter was further subjected to N -alkylation and N -arylation reactions. All resulting compounds showed potent inhibition of I, II and particularly of cancer-related IX and XII isoforms of human carbonic anhydrase.

Key concepts: Sulfonamide, Chemistry, Carbonic anhydrase, Carbonic Anhydrase I, Pyrazole, Diazo, Alkylation, Primary (astronomy)

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