TY - JOUR
T1 - Synthesis and antimycobacterial activity of 4-(5-substituted-1,3,4-oxadiazol-2-yl)pyridines
AU - Navarrete-Vázquez, Gabriel
AU - Molina-Salinas, Gloria María
AU - Duarte-Fajardo, Zetel Vahi
AU - Vargas-Villarreal, Javier
AU - Estrada-Soto, Samuel
AU - González-Salazar, Francisco
AU - Hernández-Núñez, Emanuel
AU - Said-Fernández, Salvador
N1 - 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.
PY - 2007/8/15
Y1 - 2007/8/15
N2 - 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.
AB - 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.
UR - https://www.scopus.com/pages/publications/34250698570
UR - https://www.scopus.com/pages/publications/34250698570#tab=citedBy
UR - https://www.mendeley.com/catalogue/7d52c01e-cef9-3412-9133-437dcda870b3/
U2 - 10.1016/j.bmc.2007.05.053
DO - 10.1016/j.bmc.2007.05.053
M3 - Article
SN - 0968-0896
VL - 15
SP - 5502
EP - 5508
JO - Bioorganic and Medicinal Chemistry
JF - Bioorganic and Medicinal Chemistry
IS - 16
ER -
