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2-Difluoromethylpyridine as a bioisosteric replacement of pyridine-N-oxide: the case of quorum sensing inhibitors

Herein, we demonstrate that 2-difluoromethylpyridine is a bioisosteric replacement of pyridine-N-oxide. Using the quorum sensing inhibitor 4NPO as a model compound, a library of 2-difluoromethylpyridine derivatives was designed, synthesized, and evaluated toward quorum sensing activity, biofilm form...

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Main Authors: Truong Thanh Tung, Thang Nguyen Quoc
Format: Bài trích
Language:English
Published: RSC Medicinal Chemistry 2021
Online Access:https://pubs.rsc.org/en/content/articlelanding/2021/MD/D1MD00245G
https://dlib.phenikaa-uni.edu.vn/handle/PNK/3295
https://doi.org/10.1039/D1MD00245G
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spelling oai:localhost:PNK-32952022-08-17T05:54:45Z 2-Difluoromethylpyridine as a bioisosteric replacement of pyridine-N-oxide: the case of quorum sensing inhibitors Truong Thanh Tung Thang Nguyen Quoc Herein, we demonstrate that 2-difluoromethylpyridine is a bioisosteric replacement of pyridine-N-oxide. Using the quorum sensing inhibitor 4NPO as a model compound, a library of 2-difluoromethylpyridine derivatives was designed, synthesized, and evaluated toward quorum sensing activity, biofilm formation, anti-violacein activity, and protease activity. As a result, compounds 1 (IC50 of 35 ± 1.12 μM), 5 (IC50 of 19 ± 1.01 μM), and 6 (IC50 of 27 ± 0.67 μM) showed a similar or better activity in comparison to 4NPO (IC50 of 33 ± 1.12 μM) in a quorum sensing system of Pseudomonas aeruginosa. In addition, compounds 1, 5, 6, and 4NPO showed good antibiofilm biomass of Pseudomonas aeruginosa and reduced violacein production in Chromobacterium violaceum. In terms of protease activity, compounds 1, 5, and 6 showed significant activity compared to 4NPO. Overall, the replacement of pyridine-N-oxide by 2-difluoromethylpyridine enhances the activity of the model compound, which could open a new path for bioisosteric replacement in drug discovery and development. 2021-10-27T02:05:04Z 2021-10-27T02:05:04Z 2021 Bài trích https://pubs.rsc.org/en/content/articlelanding/2021/MD/D1MD00245G https://dlib.phenikaa-uni.edu.vn/handle/PNK/3295 https://doi.org/10.1039/D1MD00245G en RSC Medicinal Chemistry
institution Digital Phenikaa
collection Digital Phenikaa
language English
description Herein, we demonstrate that 2-difluoromethylpyridine is a bioisosteric replacement of pyridine-N-oxide. Using the quorum sensing inhibitor 4NPO as a model compound, a library of 2-difluoromethylpyridine derivatives was designed, synthesized, and evaluated toward quorum sensing activity, biofilm formation, anti-violacein activity, and protease activity. As a result, compounds 1 (IC50 of 35 ± 1.12 μM), 5 (IC50 of 19 ± 1.01 μM), and 6 (IC50 of 27 ± 0.67 μM) showed a similar or better activity in comparison to 4NPO (IC50 of 33 ± 1.12 μM) in a quorum sensing system of Pseudomonas aeruginosa. In addition, compounds 1, 5, 6, and 4NPO showed good antibiofilm biomass of Pseudomonas aeruginosa and reduced violacein production in Chromobacterium violaceum. In terms of protease activity, compounds 1, 5, and 6 showed significant activity compared to 4NPO. Overall, the replacement of pyridine-N-oxide by 2-difluoromethylpyridine enhances the activity of the model compound, which could open a new path for bioisosteric replacement in drug discovery and development.
format Bài trích
author Truong Thanh Tung
Thang Nguyen Quoc
spellingShingle Truong Thanh Tung
Thang Nguyen Quoc
2-Difluoromethylpyridine as a bioisosteric replacement of pyridine-N-oxide: the case of quorum sensing inhibitors
author_facet Truong Thanh Tung
Thang Nguyen Quoc
author_sort Truong Thanh Tung
title 2-Difluoromethylpyridine as a bioisosteric replacement of pyridine-N-oxide: the case of quorum sensing inhibitors
title_short 2-Difluoromethylpyridine as a bioisosteric replacement of pyridine-N-oxide: the case of quorum sensing inhibitors
title_full 2-Difluoromethylpyridine as a bioisosteric replacement of pyridine-N-oxide: the case of quorum sensing inhibitors
title_fullStr 2-Difluoromethylpyridine as a bioisosteric replacement of pyridine-N-oxide: the case of quorum sensing inhibitors
title_full_unstemmed 2-Difluoromethylpyridine as a bioisosteric replacement of pyridine-N-oxide: the case of quorum sensing inhibitors
title_sort 2-difluoromethylpyridine as a bioisosteric replacement of pyridine-n-oxide: the case of quorum sensing inhibitors
publisher RSC Medicinal Chemistry
publishDate 2021
url https://pubs.rsc.org/en/content/articlelanding/2021/MD/D1MD00245G
https://dlib.phenikaa-uni.edu.vn/handle/PNK/3295
https://doi.org/10.1039/D1MD00245G
_version_ 1751856269284605952
score 8.891145

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