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 journalArticlepeer-review

117 Citations (Scopus)


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 languageEnglish
Pages (from-to)5502-5508
Number of pages7
JournalBioorganic and Medicinal Chemistry
Issue number16
Publication statusPublished - 15 Aug 2007
Externally publishedYes

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 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


Dive into the research topics of 'Synthesis and antimycobacterial activity of 4-(5-substituted-1,3,4-oxadiazol-2-yl)pyridines'. Together they form a unique fingerprint.

Cite this