Synthesis and antimycobacterial activity of 4-(5-substituted-1,3,4-oxadiazol-2-yl)pyridines |
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Authors: | 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 |
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Affiliation: | Facultad de Farmacia, Universidad Autónoma del Estado de Morelos, Cuernavaca, Morelos 62210, Mexico. gabriel-navarrete@uaem.mx |
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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 H(37)Rv 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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