Background: Oxadiazole derivatives are the biologically active heterocyclic compounds. Thus, we synthesized a series of Mannich bases, 3-(arylaminomethyl)-5-(pyridin- 4-yl)-1,3,4-oxadiazole-(3H)-thi-2-one derivatives(3a-3g) were synthesized from Isoniazid [INH (1)], a first line antimycobacterial drug, and these compounds were evaluated as antimycobacterial agents.
Methods: The INH was reacted with potassium hydroxide and carbon disulfide to give 5-(pyridin- 4-yl)-1,3,4-oxadiazole-2(3H)-thione (2), followed by reacting compound 2 with appropriate aromatic amines in the presence of formaldehyde to obtain desired compounds (3a-3g). The structures of these compounds have been established by IR, 1H-NMR, Mass spectral and elemental analysis. These synthesized compounds (3a-3g) were evaluated for their antimycobacterial activity against M. tuberculosis H37Rv strain.
Results: All the synthesized compounds (3a-3g) exhibited antimycobacterial activity and were compared to reference drugs Streptomycin (MIC value of 6.25μg/mL), INH (MIC value of 3.125μg/mL) and pyrazinamide (MIC value of 3.125μg/mL). Compounds 3c and 3e exhibited the most promising antimycobacterial activity.
Conclusion: All the title compounds were synthesized and exhibited promising antimycobacterial activity against M. tuberculosis H37Rv strain.
[http://dx.doi.org/10.1001/jama.282.7.677] [PMID: 10517722]
[http://dx.doi.org/10.1016/j.ejmech.2010.01.023] [PMID: 20149501]
[http://dx.doi.org/10.1016/S1074-5521(00)00006-5] [PMID: 11048950]
[http://dx.doi.org/10.1016/j.ejmech.2007.05.002] [PMID: 17673337]
[http://dx.doi.org/10.1016/j.bmcl.2008.08.006] [PMID: 18725179]
[http://dx.doi.org/10.1016/j.bmc.2006.09.067] [PMID: 17064907]
[http://dx.doi.org/10.1016/j.bmcl.2009.08.046] [PMID: 19729303]
[http://dx.doi.org/10.1016/j.bmcl.2005.08.081] [PMID: 16183276]