Synthesis and antimycobacterial activity of 4-(5-substituted-1,3,4-oxadiazol-2-yl)pyridines

Gabriel Navarrete-Vázquez; Gloria María Molina-Salinas; Zetel Vahi Duarte-Fajardo; Javier Vargas-Villarreal; Samuel Estrada-Soto; Francisco González-Salazar; Emanuel Hernández-Núñez; Salvador Said-Fernández

doi:10.1016/j.bmc.2007.05.053

Synthesis and antimycobacterial activity of 4-(5-substituted-1,3,4-oxadiazol-2-yl)pyridines

Gabriel Navarrete-Vázquez, Gloria María Molina-Salinas, Zetel Vahi Duarte-Fajardo, Javier Vargas-Villarreal, Samuel Estrada-Soto, Francisco González-Salazar, Emanuel Hernández-Núñez, Salvador Said-Fernández

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119 Citations (Scopus)

Abstract

4-(5-Substituted-1,3,4-oxadiazol-2-yl)pyridine derivatives 1-12 were synthesized and evaluated for their in vitro antimycobacterial activity. Some compounds showed an interesting activity against Mycobacterium tuberculosis H ₃₇Rv and five clinical isolates (drug-sensitive and -resistant strains). Compound 4 [4-(5-pentadecyl-1,3,4-oxadiazol-2-yl)pyridine] was 10 times more active than isoniazid, 20 times more active than streptomycin, and 28 times more potent than ethambutol against drug-resistant strain CIBIN 112. Compound 5 [4-(5-heptadecyl-1,3,4-oxadiazol-2-yl)pyridine] showed the same behavior as compound 4. Both of the above structures bear a high lipophilic chain bonded to the 5-position of the oxadiazole moiety. This fact implies that there exists a contribution of lipophilicity, which could facilitate the entrance of these molecules through lipid-enriched bacterial cell membrane.

Original language	English
Pages (from-to)	5502-5508
Number of pages	7
Journal	Bioorganic and Medicinal Chemistry
Volume	15
Issue number	16
DOIs	https://doi.org/10.1016/j.bmc.2007.05.053
Publication status	Published - 15 Aug 2007
Externally published	Yes

Bibliographical note

Funding Information:
This work was supported in part by grant from PROMEP-SEP, UAEMOR-PTC-131 (GNV). ZVDF acknowledges the fellowship awarded by CONACyT to carry out graduate studies. We also thank Juan Carlos Barbosa-Ordaz from Facultad de Farmacia, UAEM, for his technical assistance. We also express our thanks to Dr. Thomas Scior from Benemérita Universidad Autónoma de Puebla for his helpful discussion.

Copyright:
Copyright 2009 Elsevier B.V., All rights reserved.

All Science Journal Classification (ASJC) codes

Biochemistry
Molecular Medicine
Molecular Biology
Pharmaceutical Science
Drug Discovery
Clinical Biochemistry
Organic Chemistry

UN SDGs

This output contributes to the following UN Sustainable Development Goals (SDGs)

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Navarrete-Vázquez, G., Molina-Salinas, G. M., Duarte-Fajardo, Z. V., Vargas-Villarreal, J., Estrada-Soto, S., González-Salazar, F., Hernández-Núñez, E., & Said-Fernández, S. (2007). Synthesis and antimycobacterial activity of 4-(5-substituted-1,3,4-oxadiazol-2-yl)pyridines. Bioorganic and Medicinal Chemistry, 15(16), 5502-5508. https://doi.org/10.1016/j.bmc.2007.05.053

@article{58675d10a22742f08da5682ce15a7bf0,

title = "Synthesis and antimycobacterial activity of 4-(5-substituted-1,3,4-oxadiazol-2-yl)pyridines",

abstract = "4-(5-Substituted-1,3,4-oxadiazol-2-yl)pyridine derivatives 1-12 were synthesized and evaluated for their in vitro antimycobacterial activity. Some compounds showed an interesting activity against Mycobacterium tuberculosis H 37Rv and five clinical isolates (drug-sensitive and -resistant strains). Compound 4 [4-(5-pentadecyl-1,3,4-oxadiazol-2-yl)pyridine] was 10 times more active than isoniazid, 20 times more active than streptomycin, and 28 times more potent than ethambutol against drug-resistant strain CIBIN 112. Compound 5 [4-(5-heptadecyl-1,3,4-oxadiazol-2-yl)pyridine] showed the same behavior as compound 4. Both of the above structures bear a high lipophilic chain bonded to the 5-position of the oxadiazole moiety. This fact implies that there exists a contribution of lipophilicity, which could facilitate the entrance of these molecules through lipid-enriched bacterial cell membrane.",

author = "Gabriel Navarrete-V{\'a}zquez and Molina-Salinas, {Gloria Mar{\'i}a} and Duarte-Fajardo, {Zetel Vahi} and Javier Vargas-Villarreal and Samuel Estrada-Soto and Francisco Gonz{\'a}lez-Salazar and Emanuel Hern{\'a}ndez-N{\'u}{\~n}ez and Salvador Said-Fern{\'a}ndez",

note = "Funding Information: This work was supported in part by grant from PROMEP-SEP, UAEMOR-PTC-131 (GNV). ZVDF acknowledges the fellowship awarded by CONACyT to carry out graduate studies. We also thank Juan Carlos Barbosa-Ordaz from Facultad de Farmacia, UAEM, for his technical assistance. We also express our thanks to Dr. Thomas Scior from Benem{\'e}rita Universidad Aut{\'o}noma de Puebla for his helpful discussion. Copyright: Copyright 2009 Elsevier B.V., All rights reserved.",

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Navarrete-Vázquez, G, Molina-Salinas, GM, Duarte-Fajardo, ZV, Vargas-Villarreal, J, Estrada-Soto, S, González-Salazar, F, Hernández-Núñez, E & Said-Fernández, S 2007, 'Synthesis and antimycobacterial activity of 4-(5-substituted-1,3,4-oxadiazol-2-yl)pyridines', Bioorganic and Medicinal Chemistry, vol. 15, no. 16, pp. 5502-5508. https://doi.org/10.1016/j.bmc.2007.05.053

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T1 - Synthesis and antimycobacterial activity of 4-(5-substituted-1,3,4-oxadiazol-2-yl)pyridines

AU - Navarrete-Vázquez, Gabriel

AU - Molina-Salinas, Gloria María

AU - Duarte-Fajardo, Zetel Vahi

AU - Vargas-Villarreal, Javier

AU - Estrada-Soto, Samuel

AU - González-Salazar, Francisco

AU - Hernández-Núñez, Emanuel

AU - Said-Fernández, Salvador

N1 - Funding Information: This work was supported in part by grant from PROMEP-SEP, UAEMOR-PTC-131 (GNV). ZVDF acknowledges the fellowship awarded by CONACyT to carry out graduate studies. We also thank Juan Carlos Barbosa-Ordaz from Facultad de Farmacia, UAEM, for his technical assistance. We also express our thanks to Dr. Thomas Scior from Benemérita Universidad Autónoma de Puebla for his helpful discussion. Copyright: Copyright 2009 Elsevier B.V., All rights reserved.

PY - 2007/8/15

Y1 - 2007/8/15

N2 - 4-(5-Substituted-1,3,4-oxadiazol-2-yl)pyridine derivatives 1-12 were synthesized and evaluated for their in vitro antimycobacterial activity. Some compounds showed an interesting activity against Mycobacterium tuberculosis H 37Rv and five clinical isolates (drug-sensitive and -resistant strains). Compound 4 [4-(5-pentadecyl-1,3,4-oxadiazol-2-yl)pyridine] was 10 times more active than isoniazid, 20 times more active than streptomycin, and 28 times more potent than ethambutol against drug-resistant strain CIBIN 112. Compound 5 [4-(5-heptadecyl-1,3,4-oxadiazol-2-yl)pyridine] showed the same behavior as compound 4. Both of the above structures bear a high lipophilic chain bonded to the 5-position of the oxadiazole moiety. This fact implies that there exists a contribution of lipophilicity, which could facilitate the entrance of these molecules through lipid-enriched bacterial cell membrane.

AB - 4-(5-Substituted-1,3,4-oxadiazol-2-yl)pyridine derivatives 1-12 were synthesized and evaluated for their in vitro antimycobacterial activity. Some compounds showed an interesting activity against Mycobacterium tuberculosis H 37Rv and five clinical isolates (drug-sensitive and -resistant strains). Compound 4 [4-(5-pentadecyl-1,3,4-oxadiazol-2-yl)pyridine] was 10 times more active than isoniazid, 20 times more active than streptomycin, and 28 times more potent than ethambutol against drug-resistant strain CIBIN 112. Compound 5 [4-(5-heptadecyl-1,3,4-oxadiazol-2-yl)pyridine] showed the same behavior as compound 4. Both of the above structures bear a high lipophilic chain bonded to the 5-position of the oxadiazole moiety. This fact implies that there exists a contribution of lipophilicity, which could facilitate the entrance of these molecules through lipid-enriched bacterial cell membrane.

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Synthesis and antimycobacterial activity of 4-(5-substituted-1,3,4-oxadiazol-2-yl)pyridines

Abstract

Bibliographical note

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UN SDGs

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