Standard

Unprotected primary sulfonamide group facilitates ring-forming cascade en route to polycyclic [1,4]oxazepine-based carbonic anhydrase inhibitors. / Sapegin, Alexander; Kalinin, Stanislav; Angeli, Andrea; Supuran, Claudiu T.; Krasavin, Mikhail.

в: Bioorganic Chemistry, Том 76, 01.02.2018, стр. 140-146.

Результаты исследований: Научные публикации в периодических изданиях › статья › Рецензирование

Harvard

Sapegin, A, Kalinin, S, Angeli, A, Supuran, CT & Krasavin, M 2018, 'Unprotected primary sulfonamide group facilitates ring-forming cascade en route to polycyclic [1,4]oxazepine-based carbonic anhydrase inhibitors', Bioorganic Chemistry, Том. 76, стр. 140-146. https://doi.org/10.1016/j.bioorg.2017.11.014

APA

Sapegin, A., Kalinin, S., Angeli, A., Supuran, C. T., & Krasavin, M. (2018). Unprotected primary sulfonamide group facilitates ring-forming cascade en route to polycyclic [1,4]oxazepine-based carbonic anhydrase inhibitors. Bioorganic Chemistry, 76, 140-146. https://doi.org/10.1016/j.bioorg.2017.11.014

Vancouver

Sapegin A, Kalinin S, Angeli A, Supuran CT, Krasavin M. Unprotected primary sulfonamide group facilitates ring-forming cascade en route to polycyclic [1,4]oxazepine-based carbonic anhydrase inhibitors. Bioorganic Chemistry. 2018 Февр. 1;76:140-146. https://doi.org/10.1016/j.bioorg.2017.11.014

Author

Sapegin, Alexander ; Kalinin, Stanislav ; Angeli, Andrea ; Supuran, Claudiu T. ; Krasavin, Mikhail. / Unprotected primary sulfonamide group facilitates ring-forming cascade en route to polycyclic [1,4]oxazepine-based carbonic anhydrase inhibitors. в: Bioorganic Chemistry. 2018 ; Том 76. стр. 140-146.

BibTeX

@article{e2b6e2ba60634d9f897cfecbd245d447,
title = "Unprotected primary sulfonamide group facilitates ring-forming cascade en route to polycyclic [1,4]oxazepine-based carbonic anhydrase inhibitors",
abstract = "4-Chloro-3-nitrobenzenesulfonamide reacted cleanly at room-temperature with a range of bis-electrophilic phenols bearing an NH-acidic functionality (secondary carboxamide or pyrazole) in the ortho-position. This produced a novel class of [1,4]oxazepine-based primary sulfonamides which exhibited strong inhibition of therapeutically relevant human carbonic anhydrases. 2-Chloronitrobenzene did not enter a similar cyclocondensation process, even under prolonged heating. Thus, the primary sulfonamide functionality plays a dual role by enabling the [1,4]oxazepine ring construction and acting as a enzyme prosthetic zinc-binding group when the resulting [1,4]oxazepine sulfonamides are employed as carbonic anhydrase inhibitors.",
keywords = "Carbonic anhydrase inhibitors, Electron-withdrawing group, Isoform-selectivity, Nucleophilic aromatic substitution, Primary sulfonamide, Reactivity-matched substrates, SMILES rearrangement, ACTIVE-SITE, STRATEGY, STRUCTURALLY DIVERSE, DENITROCYCLIZATION, SULFOCHLORINATION, ASTROCYTES, PROFILE, BENZENESULFONAMIDES, CONSTRUCTION, AGENTS",
author = "Alexander Sapegin and Stanislav Kalinin and Andrea Angeli and Supuran, {Claudiu T.} and Mikhail Krasavin",
year = "2018",
month = feb,
day = "1",
doi = "10.1016/j.bioorg.2017.11.014",
language = "English",
volume = "76",
pages = "140--146",
journal = "Bioorganic Chemistry",
issn = "0045-2068",
publisher = "Elsevier",

}

RIS

TY - JOUR

T1 - Unprotected primary sulfonamide group facilitates ring-forming cascade en route to polycyclic [1,4]oxazepine-based carbonic anhydrase inhibitors

AU - Sapegin, Alexander

AU - Kalinin, Stanislav

AU - Angeli, Andrea

AU - Supuran, Claudiu T.

AU - Krasavin, Mikhail

PY - 2018/2/1

Y1 - 2018/2/1

N2 - 4-Chloro-3-nitrobenzenesulfonamide reacted cleanly at room-temperature with a range of bis-electrophilic phenols bearing an NH-acidic functionality (secondary carboxamide or pyrazole) in the ortho-position. This produced a novel class of [1,4]oxazepine-based primary sulfonamides which exhibited strong inhibition of therapeutically relevant human carbonic anhydrases. 2-Chloronitrobenzene did not enter a similar cyclocondensation process, even under prolonged heating. Thus, the primary sulfonamide functionality plays a dual role by enabling the [1,4]oxazepine ring construction and acting as a enzyme prosthetic zinc-binding group when the resulting [1,4]oxazepine sulfonamides are employed as carbonic anhydrase inhibitors.

AB - 4-Chloro-3-nitrobenzenesulfonamide reacted cleanly at room-temperature with a range of bis-electrophilic phenols bearing an NH-acidic functionality (secondary carboxamide or pyrazole) in the ortho-position. This produced a novel class of [1,4]oxazepine-based primary sulfonamides which exhibited strong inhibition of therapeutically relevant human carbonic anhydrases. 2-Chloronitrobenzene did not enter a similar cyclocondensation process, even under prolonged heating. Thus, the primary sulfonamide functionality plays a dual role by enabling the [1,4]oxazepine ring construction and acting as a enzyme prosthetic zinc-binding group when the resulting [1,4]oxazepine sulfonamides are employed as carbonic anhydrase inhibitors.

KW - Carbonic anhydrase inhibitors

KW - Electron-withdrawing group

KW - Isoform-selectivity

KW - Nucleophilic aromatic substitution

KW - Primary sulfonamide

KW - Reactivity-matched substrates

KW - SMILES rearrangement

KW - ACTIVE-SITE

KW - STRATEGY

KW - STRUCTURALLY DIVERSE

KW - DENITROCYCLIZATION

KW - SULFOCHLORINATION

KW - ASTROCYTES

KW - PROFILE

KW - BENZENESULFONAMIDES

KW - CONSTRUCTION

KW - AGENTS

UR - http://www.scopus.com/inward/record.url?scp=85034752183&partnerID=8YFLogxK

U2 - 10.1016/j.bioorg.2017.11.014

DO - 10.1016/j.bioorg.2017.11.014

M3 - Article

AN - SCOPUS:85034752183

VL - 76

SP - 140

EP - 146

JO - Bioorganic Chemistry

JF - Bioorganic Chemistry

SN - 0045-2068

ER -

ID: 18361408