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Direct assembly of N-sulfamoyl lactam scaffolds bearing a zinc-binding group for inhibiting metalloenzymes based on desymmetrization of sulfamide and the Castagnoli-Cushman reaction. / Карчуганова, Елизавета Максимовна; Мартынова, София Дмитриевна; Калинин, Станислав Алексеевич; Angeli, Andrea; Дарьин, Дмитрий Викторович; Vullo, Daniela; Supuran, Claudiu T.; Бакулина, Ольга Юрьевна.

In: Tetrahedron, Vol. 154, 133890, 25.03.2024.

Research output: Contribution to journal › Article › peer-review

Harvard

Карчуганова, ЕМ, Мартынова, СД, Калинин, СА, Angeli, A, Дарьин, ДВ, Vullo, D, Supuran, CT & Бакулина, ОЮ 2024, 'Direct assembly of N-sulfamoyl lactam scaffolds bearing a zinc-binding group for inhibiting metalloenzymes based on desymmetrization of sulfamide and the Castagnoli-Cushman reaction', Tetrahedron, vol. 154, 133890. https://doi.org/10.1016/j.tet.2024.133890

APA

Карчуганова, Е. М., Мартынова, С. Д., Калинин, С. А., Angeli, A., Дарьин, Д. В., Vullo, D., Supuran, C. T., & Бакулина, О. Ю. (2024). Direct assembly of N-sulfamoyl lactam scaffolds bearing a zinc-binding group for inhibiting metalloenzymes based on desymmetrization of sulfamide and the Castagnoli-Cushman reaction. Tetrahedron, 154, [133890]. https://doi.org/10.1016/j.tet.2024.133890

Vancouver

Карчуганова ЕМ, Мартынова СД, Калинин СА, Angeli A, Дарьин ДВ, Vullo D et al. Direct assembly of N-sulfamoyl lactam scaffolds bearing a zinc-binding group for inhibiting metalloenzymes based on desymmetrization of sulfamide and the Castagnoli-Cushman reaction. Tetrahedron. 2024 Mar 25;154. 133890. https://doi.org/10.1016/j.tet.2024.133890

Author

Карчуганова, Елизавета Максимовна ; Мартынова, София Дмитриевна ; Калинин, Станислав Алексеевич ; Angeli, Andrea ; Дарьин, Дмитрий Викторович ; Vullo, Daniela ; Supuran, Claudiu T. ; Бакулина, Ольга Юрьевна. / Direct assembly of N-sulfamoyl lactam scaffolds bearing a zinc-binding group for inhibiting metalloenzymes based on desymmetrization of sulfamide and the Castagnoli-Cushman reaction. In: Tetrahedron. 2024 ; Vol. 154.

BibTeX

@article{bb47739546b14518a35eef24c39ceeb7,
title = "Direct assembly of N-sulfamoyl lactam scaffolds bearing a zinc-binding group for inhibiting metalloenzymes based on desymmetrization of sulfamide and the Castagnoli-Cushman reaction",
abstract = "Sulfamide was desymmetrized by a reaction with aldehydes to give N -sulfamoylimines. The latter reagents were successfully introduced into diastereo- and chemoselective transformation with cyclic anhydride using the Castagnoli-Cushman reaction to give unprotected N -sulfamoyl tetrahydroisoquinolonic (THIQ) acids under simple metal-free protocol. Thereby, the first general approach to the direct assembly of six-membered N -sulfamoyl lactams was developed. The synthesized compounds belong to representative, drug-like chemotypes with their well-defined three-dimensional structures and tunable physicochemical properties. In an attempt to probe their pharmacological potential, the newly synthesized lactams were screened against therapeutically relevant human and bacterial carbonic anhydrases, with some derivatives showing low micromolar enzyme inhibitory profiles.",
author = "Карчуганова, {Елизавета Максимовна} and Мартынова, {София Дмитриевна} and Калинин, {Станислав Алексеевич} and Andrea Angeli and Дарьин, {Дмитрий Викторович} and Daniela Vullo and Supuran, {Claudiu T.} and Бакулина, {Ольга Юрьевна}",
year = "2024",
month = mar,
day = "25",
doi = "10.1016/j.tet.2024.133890",
language = "English",
volume = "154",
journal = "Tetrahedron",
issn = "0040-4020",
publisher = "Elsevier",

}

RIS

TY - JOUR

T1 - Direct assembly of N-sulfamoyl lactam scaffolds bearing a zinc-binding group for inhibiting metalloenzymes based on desymmetrization of sulfamide and the Castagnoli-Cushman reaction

AU - Карчуганова, Елизавета Максимовна

AU - Мартынова, София Дмитриевна

AU - Калинин, Станислав Алексеевич

AU - Angeli, Andrea

AU - Дарьин, Дмитрий Викторович

AU - Vullo, Daniela

AU - Supuran, Claudiu T.

AU - Бакулина, Ольга Юрьевна

PY - 2024/3/25

Y1 - 2024/3/25

N2 - Sulfamide was desymmetrized by a reaction with aldehydes to give N -sulfamoylimines. The latter reagents were successfully introduced into diastereo- and chemoselective transformation with cyclic anhydride using the Castagnoli-Cushman reaction to give unprotected N -sulfamoyl tetrahydroisoquinolonic (THIQ) acids under simple metal-free protocol. Thereby, the first general approach to the direct assembly of six-membered N -sulfamoyl lactams was developed. The synthesized compounds belong to representative, drug-like chemotypes with their well-defined three-dimensional structures and tunable physicochemical properties. In an attempt to probe their pharmacological potential, the newly synthesized lactams were screened against therapeutically relevant human and bacterial carbonic anhydrases, with some derivatives showing low micromolar enzyme inhibitory profiles.

AB - Sulfamide was desymmetrized by a reaction with aldehydes to give N -sulfamoylimines. The latter reagents were successfully introduced into diastereo- and chemoselective transformation with cyclic anhydride using the Castagnoli-Cushman reaction to give unprotected N -sulfamoyl tetrahydroisoquinolonic (THIQ) acids under simple metal-free protocol. Thereby, the first general approach to the direct assembly of six-membered N -sulfamoyl lactams was developed. The synthesized compounds belong to representative, drug-like chemotypes with their well-defined three-dimensional structures and tunable physicochemical properties. In an attempt to probe their pharmacological potential, the newly synthesized lactams were screened against therapeutically relevant human and bacterial carbonic anhydrases, with some derivatives showing low micromolar enzyme inhibitory profiles.

UR - https://www.mendeley.com/catalogue/648544b2-6f7c-3047-8557-498b4812136b/

U2 - 10.1016/j.tet.2024.133890

DO - 10.1016/j.tet.2024.133890

M3 - Article

VL - 154

JO - Tetrahedron

JF - Tetrahedron

SN - 0040-4020

M1 - 133890

ER -

ID: 117249451