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A new way of synthesizing heterocyclic primary sulfonamide probes for carbonic anhydrase. / Кривовичева, Василиса Сергеевна; Бубырев, Андрей Иванович; Калинин, Станислав Алексеевич; Дарьин, Дмитрий Викторович; Гуреев, Максим Александрович; Vullo, Daniela; Красавин, Михаил Юрьевич; Корсаков, Михаил Константинович; Supuran, Claudiu T.

In: Mendeleev Communications, Vol. 33, No. 3, 01.05.2023, p. 325-327.

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@article{ba162331f89b4fc181ca77ad3eed08ac,
title = "A new way of synthesizing heterocyclic primary sulfonamide probes for carbonic anhydrase",
abstract = "An N,N-bis(p-methoxybenzyl)-protected a a a-acetyl-a a a-diazomethane 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 = "1,2,3-thiadiazoles, Chan–Evans–Lam arylation, Lawesson{\textquoteright} reagent, [3 + 2] dipolar cycloaddition, methyl propiolate, pyrazoles, α-acetyl-α-diazomethane sulfonamide",
author = "Кривовичева, {Василиса Сергеевна} and Бубырев, {Андрей Иванович} and Калинин, {Станислав Алексеевич} and Дарьин, {Дмитрий Викторович} and Гуреев, {Максим Александрович} and Daniela Vullo and Красавин, {Михаил Юрьевич} and Корсаков, {Михаил Константинович} and Supuran, {Claudiu T.}",
year = "2023",
month = may,
day = "1",
doi = "10.1016/j.mencom.2023.04.009",
language = "English",
volume = "33",
pages = "325--327",
journal = "Mendeleev Communications",
issn = "0959-9436",
publisher = "Elsevier",
number = "3",

}

RIS

TY - JOUR

T1 - A new way of synthesizing heterocyclic primary sulfonamide probes for carbonic anhydrase

AU - Кривовичева, Василиса Сергеевна

AU - Бубырев, Андрей Иванович

AU - Калинин, Станислав Алексеевич

AU - Дарьин, Дмитрий Викторович

AU - Гуреев, Максим Александрович

AU - Vullo, Daniela

AU - Красавин, Михаил Юрьевич

AU - Корсаков, Михаил Константинович

AU - Supuran, Claudiu T.

PY - 2023/5/1

Y1 - 2023/5/1

N2 - An N,N-bis(p-methoxybenzyl)-protected a a a-acetyl-a a a-diazomethane 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.

AB - An N,N-bis(p-methoxybenzyl)-protected a a a-acetyl-a a a-diazomethane 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.

KW - 1,2,3-thiadiazoles

KW - Chan–Evans–Lam arylation

KW - Lawesson’ reagent

KW - [3 + 2] dipolar cycloaddition

KW - methyl propiolate

KW - pyrazoles

KW - α-acetyl-α-diazomethane sulfonamide

UR - https://www.mendeley.com/catalogue/378962c7-89d3-34e1-b57c-ef81c5890b12/

U2 - 10.1016/j.mencom.2023.04.009

DO - 10.1016/j.mencom.2023.04.009

M3 - Article

VL - 33

SP - 325

EP - 327

JO - Mendeleev Communications

JF - Mendeleev Communications

SN - 0959-9436

IS - 3

ER -

ID: 113686004