Archiv der Pharmazie, volume 354, issue 2, pages 2000199
Synthesis, in vitro antibacterial activity against Mycobacterium tuberculosis, and reverse docking-based target fishing of 1,4-benzoxazin-2-one derivatives
Publication type: Journal Article
Publication date: 2020-10-14
Journal:
Archiv der Pharmazie
Quartile SCImago
Q2
Quartile WOS
Q1
Impact factor: 5.1
ISSN: 03656233, 15214184
Drug Discovery
Pharmaceutical Science
Abstract
Seventeen 1,4‐benzoxazin‐2‐ones bearing the enaminone moiety and three of their analogs were tested for the antibacterial activity against Mycobacterium tuberculosis (H37Rv). Minimal bactericidal concentrations (MBCs) were determined after 41 days of incubation by BACTEC. 1,4‐Benzoxazin‐2‐ones bearing the unsubstituted benzo moiety showed the most promising activities (MBC = 5.00 µg/ml). For most active compounds, antibacterial activities were determined daily during the 41 days. The most promising compound showed a bacteriostatic effect at a concentration of 0.31 µg/ml on Day 4 of incubation, 0.62 µg/ml on Day 6, 2.50 µg/ml on Day 9, and 5.00 µg/ml on Day 41. All studied compounds, along with some of their reported analogs, were docked to 35 proteins of M. tuberculosis to find their potent targets in these organisms. As a result of reverse docking, aspartate 1‐decarboxylase, panD, was selected as the most appropriate target. Docking of the most active compounds to mutant panD from pyrazinamide‐resistant strains of M. tuberculosis implies that they would not be active against these strains. Considering that most of pyrazinamide clinical resistance cases are due to loss‐of‐function mutations in pyrazinamidase, pncA, compounds from this study could be useful drugs for the treatment of some cases of pyrazinamide‐resistant tuberculosis.
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Wiley
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2 publications, 50%
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Pleiades Publishing
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Pleiades Publishing
1 publication, 25%
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IntechOpen
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IntechOpen, 1, 25%
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Khramtsova E. E. et al. Synthesis, in vitro antibacterial activity against Mycobacterium tuberculosis, and reverse docking-based target fishing of 1,4-benzoxazin-2-one derivatives // Archiv der Pharmazie. 2020. Vol. 354. No. 2. p. 2000199.
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Khramtsova E. E., Balandina S. Yu., Drobkova V. A., Dmitriev M. V., Mashevskaya I. V., Maslivets A. N. Synthesis, in vitro antibacterial activity against Mycobacterium tuberculosis, and reverse docking-based target fishing of 1,4-benzoxazin-2-one derivatives // Archiv der Pharmazie. 2020. Vol. 354. No. 2. p. 2000199.
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TY - JOUR
DO - 10.1002/ardp.202000199
UR - https://doi.org/10.1002%2Fardp.202000199
TI - Synthesis, in vitro antibacterial activity against Mycobacterium tuberculosis, and reverse docking-based target fishing of 1,4-benzoxazin-2-one derivatives
T2 - Archiv der Pharmazie
AU - Balandina, Svetlana Yu
AU - Drobkova, Vera A
AU - Mashevskaya, Irina V.
AU - Khramtsova, Ekaterina E
AU - Dmitriev, Maksim V
AU - Maslivets, Andrey N
PY - 2020
DA - 2020/10/14 00:00:00
PB - Wiley
SP - 2000199
IS - 2
VL - 354
SN - 0365-6233
SN - 1521-4184
ER -
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@article{2020_Khramtsova,
author = {Svetlana Yu Balandina and Vera A Drobkova and Irina V. Mashevskaya and Ekaterina E Khramtsova and Maksim V Dmitriev and Andrey N Maslivets},
title = {Synthesis, in vitro antibacterial activity against Mycobacterium tuberculosis, and reverse docking-based target fishing of 1,4-benzoxazin-2-one derivatives},
journal = {Archiv der Pharmazie},
year = {2020},
volume = {354},
publisher = {Wiley},
month = {oct},
url = {https://doi.org/10.1002%2Fardp.202000199},
number = {2},
pages = {2000199},
doi = {10.1002/ardp.202000199}
}
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Khramtsova, Ekaterina E., et al. “Synthesis, in vitro antibacterial activity against Mycobacterium tuberculosis, and reverse docking-based target fishing of 1,4-benzoxazin-2-one derivatives.” Archiv der Pharmazie, vol. 354, no. 2, Oct. 2020, p. 2000199. https://doi.org/10.1002%2Fardp.202000199.