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

100 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 languageEnglish
Pages (from-to)5502-5508
Number of pages7
JournalBioorganic and Medicinal Chemistry
Volume15
Issue number16
DOIs
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:
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

Fingerprint

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