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Pharmaceuticals, том 15, издание 2, номер публикации: 155

Synthesis and Characterization of Novel 2-Acyl-3-trifluoromethylquinoxaline 1,4-Dioxides as Potential Antimicrobial Agents

Buravchenko Galina I. 1
Alam Md Shah 3, 4, 5, 6
Grammatikova Natalia E. 1
Frolova Svetlana G. 2, 7
Vatlin Aleksey A. 2, 8
Tian Xirong 3, 4, 5, 6
Ivanov Ivan V. 1, 9
Bekker Olga B. 2
Kryakvin Maxim A. 10
Dontsova Olga A. 10, 11, 12
Danilenko Valery N. 2
Zhang Tianyu 3, 4, 5, 6
1
 
Gause Institute of New Antibiotics, 119021 Moscow, Russia
3
 
State Key Laboratory of Respiratory Disease, Guangzhou Institutes of Biomedicine and Health, Chinese Academy of Sciences, Guangzhou 510530, China
4
 
China-New Zealand Joint Laboratory on Biomedicine and Health, Guangzhou 510530, China
5
 
Guangdong-Hong Kong-Macao Joint Laboratory of Respiratory Infectious Diseases, Guangzhou Institutes of Biomedicine and Health, Chinese Academy of Sciences, Guangzhou 510530, China
6
 
University of Chinese Academy of Sciences, Beijing 100049, China
9
 
Organic Chemistry Department, Faculty of Natural Sciences, Mendeleyev University of Chemical Technology, 9 Miusskaya Square, 125190 Moscow, Russia
Тип документаJournal Article
Дата публикации2022-01-27
ИздательMultidisciplinary Digital Publishing Institute (MDPI)
Название журналаPharmaceuticals
Квартиль по SCImagoQ1
Квартиль по Web of ScienceQ1
Импакт-фактор 20215.22
ISSN14248247
Drug Discovery
Pharmaceutical Science
Molecular Medicine
Краткое описание
The emergence of drug resistance in pathogens leads to a loss of effectiveness of antimicrobials and complicates the treatment of bacterial infections. Quinoxaline 1,4-dioxides represent a prospective scaffold for search of new compounds with improved chemotherapeutic characteristics. Novel 2-acyl-3-trifluoromethylquinoxaline 1,4-dioxides with alteration of substituents at position 2 and 6 were synthesized via nucleophilic substitution with piperazine moiety and evaluated against a broad panel of bacteria and fungi by measuring their minimal inhibitory concentrations. Their mode of action was assessed by whole-genomic sequencing of spontaneous drug-resistant Mycobacterium smegmatis mutants, followed by comparative genomic analysis, and on an original pDualrep2 system. Most of the 2-acyl-3-trifluoromethylquinoxaline 1,4-dioxides showed high antibacterial properties against Gram-positive strains, including mycobacteria, and the introduction of a halogen atom in the position 6 of the quinoxaline ring further increased their activity, with 13c being the most active compound. The mode of action studies confirmed the DNA-damaging nature of the obtained quinoxaline 1,4-dioxides, while drug-resistance may be provided by mutations in redox homeostasis genes, encoding enzymes potentially involved in the activation of the compounds. This study extends views about the antimicrobial and antifungal activities of the quinoxaline 1,4-dioxides and can potentially lead to the discovery of new antibacterial drugs.
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1. Buravchenko G. I. и др. Synthesis and Characterization of Novel 2-Acyl-3-trifluoromethylquinoxaline 1,4-Dioxides as Potential Antimicrobial Agents // Pharmaceuticals. 2022. Т. 15. № 2. С. 155.
RIS |
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TY - JOUR

DO - 10.3390/ph15020155

UR - http://dx.doi.org/10.3390/ph15020155

TI - Synthesis and Characterization of Novel 2-Acyl-3-trifluoromethylquinoxaline 1,4-Dioxides as Potential Antimicrobial Agents

T2 - Pharmaceuticals

AU - Buravchenko, Galina I.

AU - Maslov, Dmitry A.

AU - Alam, Md Shah

AU - Grammatikova, Natalia E.

AU - Frolova, Svetlana G.

AU - Vatlin, Aleksey A.

AU - Tian, Xirong

AU - Ivanov, Ivan V.

AU - Bekker, Olga B.

AU - Kryakvin, Maxim A.

AU - Dontsova, Olga A.

AU - Danilenko, Valery N.

AU - Zhang, Tianyu

AU - Shchekotikhin, Andrey E.

PY - 2022

DA - 2022/01/27

PB - MDPI AG

SP - 155

IS - 2

VL - 15

SN - 1424-8247

ER -

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@article{Buravchenko_2022,

doi = {10.3390/ph15020155},

url = {https://doi.org/10.3390%2Fph15020155},

year = 2022,

month = {jan},

publisher = {{MDPI} {AG}},

volume = {15},

number = {2},

pages = {155},

author = {Galina I. Buravchenko and Dmitry A. Maslov and Md Shah Alam and Natalia E. Grammatikova and Svetlana G. Frolova and Aleksey A. Vatlin and Xirong Tian and Ivan V. Ivanov and Olga B. Bekker and Maxim A. Kryakvin and Olga A. Dontsova and Valery N. Danilenko and Tianyu Zhang and Andrey E. Shchekotikhin},

title = {Synthesis and Characterization of Novel 2-Acyl-3-trifluoromethylquinoxaline 1,4-Dioxides as Potential Antimicrobial Agents},

journal = {Pharmaceuticals}

}

MLA
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Buravchenko, Galina I., et al. “Synthesis and Characterization of Novel 2-Acyl-3-Trifluoromethylquinoxaline 1,4-Dioxides as Potential Antimicrobial Agents.” Pharmaceuticals, vol. 15, no. 2, Jan. 2022, p. 155. Crossref, https://doi.org/10.3390/ph15020155.