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A convenient synthesis of a chlorobenzothiophenyl-indole-based inhibitor of bacterial cystathionine γ-lyase

Maxim Alexandrovich Novikov 1, 2
Maxim Alexandrovich Novikov
, 
Konstantin Vladislavovich Potapov 1, 2
Konstantin Vladislavovich Potapov
, 
Roman Aleksandrovich Novikov 1, 2, 3
Roman Aleksandrovich Novikov
,  ,  , 
Sergei Nikolaevich Kochetkov 1
Sergei Nikolaevich Kochetkov
, 
Alexander Aleksandrovich Makarov 1
Alexander Aleksandrovich Makarov
, 
Vladimir Aleksandrovich Mitkevich 1, 4
Vladimir Aleksandrovich Mitkevich
1 V.A. Engelhardt Institute of Molecular Biology, Russian Academy of Sciences, Moscow, Russian Federation
3 Sirius University of Science and Technology, Sochi, Russian Federation
4 Institute of Fundamental Medicine and Biology, Kazan Federal University, Kazan, Russian Federation
10.1016/j.mencom.2024.02.030
Published 2024-02-19
Communication , Volume 34, Issue 2, 255-258
3
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Novikov M. A. et al. A convenient synthesis of a chlorobenzothiophenyl-indole-based inhibitor of bacterial cystathionine γ-lyase // Mendeleev Communications. 2024. Vol. 34. No. 2. pp. 255-258.
GOST all authors (up to 50) Copy
Novikov M. A., Potapov K. V., Novikov R. A., Solyev P. N., Tomilov Y. V., Kochetkov S. N., Makarov A. A., Mitkevich V. A. A convenient synthesis of a chlorobenzothiophenyl-indole-based inhibitor of bacterial cystathionine γ-lyase // Mendeleev Communications. 2024. Vol. 34. No. 2. pp. 255-258.
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TY - JOUR
DO - 10.1016/j.mencom.2024.02.030
UR - https://mendcomm.colab.ws/publications/10.1016/j.mencom.2024.02.030
TI - A convenient synthesis of a chlorobenzothiophenyl-indole-based inhibitor of bacterial cystathionine γ-lyase
T2 - Mendeleev Communications
AU - Novikov, Maxim Alexandrovich
AU - Potapov, Konstantin Vladislavovich
AU - Novikov, Roman Aleksandrovich
AU - Solyev, Pavel Nikolayevich
AU - Tomilov, Yury Vasil'evich
AU - Kochetkov, Sergei Nikolaevich
AU - Makarov, Alexander Aleksandrovich
AU - Mitkevich, Vladimir Aleksandrovich
PY - 2024
DA - 2024/02/19
PB - Mendeleev Communications
SP - 255-258
IS - 2
VL - 34
ER -
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@article{2024_Novikov,
author = {Maxim Alexandrovich Novikov and Konstantin Vladislavovich Potapov and Roman Aleksandrovich Novikov and Pavel Nikolayevich Solyev and Yury Vasil'evich Tomilov and Sergei Nikolaevich Kochetkov and Alexander Aleksandrovich Makarov and Vladimir Aleksandrovich Mitkevich},
title = {A convenient synthesis of a chlorobenzothiophenyl-indole-based inhibitor of bacterial cystathionine γ-lyase},
journal = {Mendeleev Communications},
year = {2024},
volume = {34},
publisher = {Mendeleev Communications},
month = {Feb},
url = {https://mendcomm.colab.ws/publications/10.1016/j.mencom.2024.02.030},
number = {2},
pages = {255--258},
doi = {10.1016/j.mencom.2024.02.030}
}
MLA
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Novikov, Maxim Alexandrovich, et al. “A convenient synthesis of a chlorobenzothiophenyl-indole-based inhibitor of bacterial cystathionine γ-lyase.” Mendeleev Communications, vol. 34, no. 2, Feb. 2024, pp. 255-258. https://mendcomm.colab.ws/publications/10.1016/j.mencom.2024.02.030.

Keywords

antibacterial compounds
antibiotics potentiation
bCSE
benzo[b]thiophenes
cross-coupling.
indole-based inhibitors
indoles
NL3

Abstract

A convenient and efficient synthesis of 3-{[6-(7-chloro- benzo[b]thiophen-2-yl)-1H-indol-1-yl]methyl}-1H-pyrazole- 5-carboxylic acid (NL3), which is currently among the most active and promising bacterial cystathionine γ-lyase (bCSE) inhibitors, has been developed. It is based on shifting the key stage of [Pd]-catalyzed cross-coupling of the indole and benzothiophene counterparts to the beginning of the synthetic scheme, with the polarity reversal of the components being coupled, to give 6-(7-chlorobenzo[b]thiophen-2-yl)-1H- indole as the key intermediate. The STD NMR method was used to estimate the NL3 compound obtained in the optimized synthesis as a ligand to saCSE (the main producer of H2S in pathogenic S. aureus).

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