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Scaffold hopping in the oxadiazole antibiotic structure leads to more active compounds

Lyubov V Vinogradova 1
Lyubov V Vinogradova
, 
Kristina Yuryevna Komarova 1
Kristina Yuryevna Komarova
, 
Mikhail Vasiljevich Chudinov 1
Mikhail Vasiljevich Chudinov
, 
Elizaveta Vladimirovna Rogacheva 2
Elizaveta Vladimirovna Rogacheva
, 
Lyudmila Aleksandrovna Kraeva 2
Lyudmila Aleksandrovna Kraeva
, 
Alexei Yur'evich Lukin 1
Alexei Yur'evich Lukin
1 M.V. Lomonosov Institute of Fine Chemical Technologies, MIREA - Russian Technological University, Moscow, Russian Federation
2 St. Petersburg Pasteur Institute, St. Petersburg, Russian Federation
10.1016/j.mencom.2024.04.016
Published 2024-04-22
Communication , Volume 34, Issue 3, 362-364
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Vinogradova L. V. et al. Scaffold hopping in the oxadiazole antibiotic structure leads to more active compounds // Mendeleev Communications. 2024. Vol. 34. No. 3. pp. 362-364.
GOST all authors (up to 50) Copy
Vinogradova L. V., Komarova K. Y., Chudinov M. V., Rogacheva E. V., Kraeva L. A., Lukin A. Y. Scaffold hopping in the oxadiazole antibiotic structure leads to more active compounds // Mendeleev Communications. 2024. Vol. 34. No. 3. pp. 362-364.
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TY - JOUR
DO - 10.1016/j.mencom.2024.04.016
UR - https://mendcomm.colab.ws/publications/10.1016/j.mencom.2024.04.016
TI - Scaffold hopping in the oxadiazole antibiotic structure leads to more active compounds
T2 - Mendeleev Communications
AU - Vinogradova, Lyubov V
AU - Komarova, Kristina Yuryevna
AU - Chudinov, Mikhail Vasiljevich
AU - Rogacheva, Elizaveta Vladimirovna
AU - Kraeva, Lyudmila Aleksandrovna
AU - Lukin, Alexei Yur'evich
PY - 2024
DA - 2024/04/22
PB - Mendeleev Communications
SP - 362-364
IS - 3
VL - 34
ER -
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@article{2024_Vinogradova,
author = {Lyubov V Vinogradova and Kristina Yuryevna Komarova and Mikhail Vasiljevich Chudinov and Elizaveta Vladimirovna Rogacheva and Lyudmila Aleksandrovna Kraeva and Alexei Yur'evich Lukin},
title = {Scaffold hopping in the oxadiazole antibiotic structure leads to more active compounds},
journal = {Mendeleev Communications},
year = {2024},
volume = {34},
publisher = {Mendeleev Communications},
month = {Apr},
url = {https://mendcomm.colab.ws/publications/10.1016/j.mencom.2024.04.016},
number = {3},
pages = {362--364},
doi = {10.1016/j.mencom.2024.04.016}
}
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Vinogradova, Lyubov V., et al. “Scaffold hopping in the oxadiazole antibiotic structure leads to more active compounds.” Mendeleev Communications, vol. 34, no. 3, Apr. 2024, pp. 362-364. https://mendcomm.colab.ws/publications/10.1016/j.mencom.2024.04.016.

Keywords

2
6-diazaspiro[3.4]octane.
antibiotic resistance
carboxamides
ESKAPE pathogens
isosteric replacement
methicillin-resistant bacteria
non-β-lactam antibiotics
organofluorine compounds

Abstract

Isosteric replacement of the oxadiazole ring by amide bond in the structure of new non-β-lactam antibiotics led to compounds with higher activity against Gram-positive pathogens of ESKAPE panel. A series of 17 compounds were synthesized by acylation of 4-(4-fluorophenoxy)aniline with various amino acids. The spirocyclic derivative with 6-methylsulfonyl-2,6-diazaspiro[3.4]octane moiety showed excellent minimum inhibitory concentrations of 0.093-0.75 μg ml−1 against a number of methicillin-resistant Staphylococcus aureus strains.

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