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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97 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 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
Publication statusPublished - 15 Aug 2007
Externally publishedYes

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