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

Research output: Contribution to journalArticle

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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 H37Rv 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. © 2007 Elsevier Ltd. All rights reserved.
Original languageEnglish
Pages (from-to)5502-5508
Number of pages7
JournalBioorganic and Medicinal Chemistry
DOIs
Publication statusPublished - 15 Aug 2007
Externally publishedYes

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Pyridines
Oxadiazoles
Ethambutol
Isoniazid
Streptomycin
Mycobacterium tuberculosis
Pharmaceutical Preparations
Cell Membrane
Cell membranes
Lipids
Derivatives
Molecules
pyridine
4-(5-pentadecyl-1,3,4-oxadiazol-2-yl)pyridine
In Vitro Techniques

Cite this

Navarrete-Vázquez, G., Molina-Salinas, G. M., Duarte-Fajardo, Z. V., Vargas-Villarreal, J., Estrada-Soto, S., González-Salazar, F., ... Said-Fernández, S. (2007). Synthesis and antimycobacterial activity of 4-(5-substituted-1,3,4-oxadiazol-2-yl)pyridines. Bioorganic and Medicinal Chemistry, 5502-5508. https://doi.org/10.1016/j.bmc.2007.05.053
Navarrete-Vázquez, Gabriel ; Molina-Salinas, Gloria María ; Duarte-Fajardo, Zetel Vahi ; Vargas-Villarreal, Javier ; Estrada-Soto, Samuel ; González-Salazar, Francisco ; Hernández-Núñez, Emanuel ; Said-Fernández, Salvador. / Synthesis and antimycobacterial activity of 4-(5-substituted-1,3,4-oxadiazol-2-yl)pyridines. In: Bioorganic and Medicinal Chemistry. 2007 ; pp. 5502-5508.
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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 H37Rv 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. {\circledC} 2007 Elsevier Ltd. All rights reserved.",
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",
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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, pp. 5502-5508. https://doi.org/10.1016/j.bmc.2007.05.053

Synthesis and antimycobacterial activity of 4-(5-substituted-1,3,4-oxadiazol-2-yl)pyridines. / Navarrete-Vázquez, Gabriel; Molina-Salinas, Gloria María; Duarte-Fajardo, Zetel Vahi; Vargas-Villarreal, Javier; Estrada-Soto, Samuel; González-Salazar, Francisco; Hernández-Núñez, Emanuel; Said-Fernández, Salvador.

In: Bioorganic and Medicinal Chemistry, 15.08.2007, p. 5502-5508.

Research output: Contribution to journalArticle

TY - JOUR

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

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 H37Rv 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. © 2007 Elsevier Ltd. All rights reserved.

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 H37Rv 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. © 2007 Elsevier Ltd. All rights reserved.

U2 - 10.1016/j.bmc.2007.05.053

DO - 10.1016/j.bmc.2007.05.053

M3 - Article

SP - 5502

EP - 5508

JO - Bioorganic and Medicinal Chemistry

JF - Bioorganic and Medicinal Chemistry

SN - 0968-0896

ER -

Navarrete-Vázquez G, Molina-Salinas GM, Duarte-Fajardo ZV, Vargas-Villarreal J, Estrada-Soto S, González-Salazar F et al. Synthesis and antimycobacterial activity of 4-(5-substituted-1,3,4-oxadiazol-2-yl)pyridines. Bioorganic and Medicinal Chemistry. 2007 Aug 15;5502-5508. https://doi.org/10.1016/j.bmc.2007.05.053