V. Krivovicheva, A. Bubyrev, S. Kalinin, D. Dar’in, M. Gureev, D. Vullo, M. Krasavin, M. Korsakov, C. T. Supuran, “A new way of synthesizing heterocyclic primary sulfonamide probes for carbonic anhydrase”, Mendeleev Commun., 2023, Volume 33, Issue 3,Pages <nobr>325

This article is cited in 1 paper

Communications

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

V. Krivovicheva^a, A. Bubyrev^a, S. Kalinin^a, D. Dar’in^a, M. Gureev^b, D. Vullo^c, M. Krasavin^ad, M. Korsakov^e, C. T. Supuran^c

^a Institute of Chemistry, St. Petersburg State University, St. Petersburg, Russian Federation
^b I.M. Sechenov First Moscow State Medical University, Moscow, Russian Federation
^c Department of Neurofarba, Universita degli Studi di Firenze, Florence, Italy
^d Immanuel Kant Baltic Federal University, Kaliningrad, Russian Federation
^e K. D. Ushinsky Yaroslavl State Pedagogical University, Yaroslavl, Russian Federation

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-1H-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.

Keywords: α-acetyl-α-diazomethane sulfonamide, methyl propiolate, [3 + 2] dipolar cycloaddition, Lawesson’ reagent, Chan–Evans–Lam arylation, pyrazoles, 1,2,3-thiadiazoles.

Language: English

DOI: 10.1016/j.mencom.2023.04.009

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