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., 33:3 (2023), 325

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Mendeleev Communications, 2023, Volume 33, Issue 3, Pages 325–327
DOI: https://doi.org/10.1016/j.mencom.2023.04.009 (Mi mendc386)

This article is cited in 2 scientific papers (total in 2 papers)

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

Full-text PDF (577 kB) Citations (2) Supplementary materials

DOI: https://doi.org/10.1016/j.mencom.2023.04.009

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

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.

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Document Type: Article

Language: English

*Supplementary materials:*
		Supplementary_data_1.pdf	(1.9 Mb)

Citation: 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., 33:3 (2023), 325–327

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https://www.mathnet.ru/eng/mendc/v33/i3/p325

This publication is cited in the following 2 articles:

Citing articles in Google Scholar: Russian citations, English citations
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