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 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.
authors.affiliation: Facultad de Farmacia, Universidad Autónoma del Estado de Morelos, Cuernavaca, Morelos 62210, Mexico. gabriel-navarrete@uaem.mx
authors.forename: Gabriel
authors.initials: G
authors.lastname: Navarrete-Vázquez
authors.forename: Gloria María
authors.initials: GM
authors.lastname: Molina-Salinas
authors.forename: Zetel Vahi
authors.initials: ZV
authors.lastname: Duarte-Fajardo
authors.forename: Javier
authors.initials: J
authors.lastname: Vargas-Villarreal
authors.forename: Samuel
authors.initials: S
authors.lastname: Estrada-Soto
authors.forename: Francisco
authors.initials: F
authors.lastname: González-Salazar
authors.forename: Emanuel
authors.initials: E
authors.lastname: Hernández-Núñez
authors.forename: Salvador
authors.initials: S
authors.lastname: Said-Fernández
mesh_terms: D000818:Animals; D000995:Antitubercular Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000633:toxicity*; D002478:Cells, Cultured; D055598:Chemical Phenomena; D002627:Chemistry, Physical; D002522:Chlorocebus aethiops; D006801:Humans; D015394:Molecular Structure; D009169:Mycobacterium tuberculosis / Q000187:drug effects / Q000302:isolation & purification; D010069:Oxadiazoles / Q000138:chemical synthesis* / Q000737:chemistry / Q000633:toxicity*; D011725:Pyridines / Q000138:chemical synthesis* / Q000737:chemistry / Q000633:toxicity*; D013329:Structure-Activity Relationship
chemical_list: D000995:Antitubercular Agents; D010069:Oxadiazoles; D011725:Pyridines; C023666:pyridine