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

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

Vasilisa Sergeevna Krivovicheva 1
Vasilisa Sergeevna Krivovicheva
, 
Andrey Ivanovich Bubyrev 1
Andrey Ivanovich Bubyrev
, 
Stanislav Alekseevich Kalinin 1
Stanislav Alekseevich Kalinin
, 
Dmitry Viktorovich Dar’in 1
Dmitry Viktorovich Dar’in
,  , 
Daniela Vullo 3
Daniela Vullo
, 
Mikhail Yur'evich Krasavin 1, 4
Mikhail Yur'evich Krasavin
, 
Mikhail K Korsakov 5
Mikhail K Korsakov
, 
Claudiu T Supuran 3
Claudiu T Supuran
1 Institute of Chemistry, St. Petersburg State University, St. Petersburg, Russian Federation
2 I.M. Sechenov First Moscow State Medical University, Moscow, Russian Federation
3 Department of Neurofarba, Universita degli Studi di Firenze, Florence, Italy
4 Immanuel Kant Baltic Federal University, Kaliningrad, Russian Federation
5 K. D. Ushinsky Yaroslavl State Pedagogical University, Yaroslavl, Russian Federation
10.1016/j.mencom.2023.04.009
Published 2023-04-13
Communication , Volume 33, Issue 3, 325-327
2
Share
Cite this
GOST
 | 
Cite this
GOST Copy
Krivovicheva V. S. et al. A new way of synthesizing heterocyclic primary sulfonamide probes for carbonic anhydrase // Mendeleev Communications. 2023. Vol. 33. No. 3. pp. 325-327.
GOST all authors (up to 50) Copy
Krivovicheva V. S., Bubyrev A. I., Kalinin S. A., Dar’in D. V., Gureev M. A., Vullo D., Krasavin M. Y., Korsakov M. K., Supuran C. T. A new way of synthesizing heterocyclic primary sulfonamide probes for carbonic anhydrase // Mendeleev Communications. 2023. Vol. 33. No. 3. pp. 325-327.
RIS
 | 
Cite this
RIS Copy
TY - JOUR
DO - 10.1016/j.mencom.2023.04.009
UR - https://mendcomm.colab.ws/publications/10.1016/j.mencom.2023.04.009
TI - A new way of synthesizing heterocyclic primary sulfonamide probes for carbonic anhydrase
T2 - Mendeleev Communications
AU - Krivovicheva, Vasilisa Sergeevna
AU - Bubyrev, Andrey Ivanovich
AU - Kalinin, Stanislav Alekseevich
AU - Dar’in, Dmitry Viktorovich
AU - Gureev, Maxim Aleksandrovich
AU - Vullo, Daniela
AU - Krasavin, Mikhail Yur'evich
AU - Korsakov, Mikhail K
AU - Supuran, Claudiu T
PY - 2023
DA - 2023/04/13
PB - Mendeleev Communications
SP - 325-327
IS - 3
VL - 33
ER -
BibTex
 | 
Cite this
BibTex (up to 50 authors) Copy
@article{2023_Krivovicheva,
author = {Vasilisa Sergeevna Krivovicheva and Andrey Ivanovich Bubyrev and Stanislav Alekseevich Kalinin and Dmitry Viktorovich Dar’in and Maxim Aleksandrovich Gureev and Daniela Vullo and Mikhail Yur'evich Krasavin and Mikhail K Korsakov and Claudiu T Supuran},
title = {A new way of synthesizing heterocyclic primary sulfonamide probes for carbonic anhydrase},
journal = {Mendeleev Communications},
year = {2023},
volume = {33},
publisher = {Mendeleev Communications},
month = {Apr},
url = {https://mendcomm.colab.ws/publications/10.1016/j.mencom.2023.04.009},
number = {3},
pages = {325--327},
doi = {10.1016/j.mencom.2023.04.009}
}
MLA
Cite this
MLA Copy
Krivovicheva, Vasilisa Sergeevna, et al. “A new way of synthesizing heterocyclic primary sulfonamide probes for carbonic anhydrase.” Mendeleev Communications, vol. 33, no. 3, Apr. 2023, pp. 325-327. https://mendcomm.colab.ws/publications/10.1016/j.mencom.2023.04.009.

Keywords

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

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.

References

.
Multiple binding modes of inhibitors to carbonic anhydrases: how to design specific drugs targeting 15 different isoforms?
Alterio V., Di Fiore A., D’Ambrosio K., Supuran C.T., De Simone G.
Chemical Reviews, 2012
.
The Chan–Evans–Lam N-Arylation of 2-Imidazolines
Dar’in D., Krasavin M.
Journal of Organic Chemistry, 2016
.
A Synthesis of (+)-Saxitoxin
Fleming J.J., Du Bois J.
Journal of the American Chemical Society, 2006
.
(+)-Saxitoxin:  A First and Second Generation Stereoselective Synthesis
Fleming J.J., McReynolds M.D., Du Bois J.
Journal of the American Chemical Society, 2007
.
Carbonic Anhydrase Inhibitors with Dual-Tail Moieties To Match the Hydrophobic and Hydrophilic Halves of the Carbonic Anhydrase Active Site
Tanpure R.P., Ren B., Peat T.S., Bornaghi L.F., Vullo D., Supuran C.T., Poulsen S.
Journal of Medicinal Chemistry, 2015
.
Metal-free Three-Component Synthesis of 1,2,3-Triazoline-4-sulfonamides
Bubyrev A., Adamchik M., Dar’in D., Kantin G., Krasavin M.
Journal of Organic Chemistry, 2021
.
Metal-Free Synthesis of 1,5-Disubstituted 1,2,3-Triazoles
Bubyrev A., Malkova K., Kantin G., Dar’in D., Krasavin M.
Journal of Organic Chemistry, 2021
.
Novel approaches for designing drugs that interfere with pH regulation
Berrino E., Supuran C.T.
Expert Opinion on Drug Discovery, 2019