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  4. Synthesis and antimycobacterial activity of some triazole derivatives – new route to functionalized triazolopyridazines

Synthesis and antimycobacterial activity of some triazole derivatives – new route to functionalized triazolopyridazines

Authors

Tehrani Kamaleddin Haj Mohammad Ebrahim
Mashayekhi, Vida
Azerang, Parisa
Minaei, Somayeh
Sardari, Soroush
Kobarfard, Farzad
Shahid Beheshti University of Medical Sciences ; , School of Pharmacy ; , Department of Medicinal Chemistry ;

Iran. J. Pharm. Res. 2015; 14 (Supp.): 59-68
IJPR-Iranian Journal of Pharmaceutical Research
Journal Country: Islamic Republic of Iran
P-ISSN: 1735-0328
E-ISSN: 1726-6890
Type of Publication: Journal Article
Type of Research: Experimental Studies
Keywords: Triazoles / Chemical Synthesis
Board Subjects: Health Systems, Pyridazines ,Anti-Bacterial Agents ,Hydrazines
Citation: Kamaleddin Haj Mohammad Ebrahim Tehrani ,Vida Mashayekhi ,Parisa Azerang ,Somayeh Minaei ,Soroush Sardari ,Farzad Kobarfard , Synthesis and antimycobacterial activity of some triazole derivatives – new route to functionalized triazolopyridazines, Iran. J. Pharm. Res. 2015; 14 (Supp.): 59-68

Abstract English

A series of cyclic analogues of bioactive thiosemicarbazide derivatives have been synthesized as potential antimycobacterial agents. The 4-amino-1, 2, 4-triazole-5-thione analogues [Ia-f] were prepared by heating a mixture of thiocarbohydrzide and appropriate carboxylic acids. Reaction of thiocarbohydrazide with gamma-ketoesters in the presence of sodium methoxide furnished triazolopyridazine derivatives IIa-b. Finally, condensation of 4-amino-1, 2, 4-triazole-5-thione with some aldehydes gave Schiff bases IIIa-e. After characterization by different spectroscopic and analytical methods, the derivatives were tested for their inhibitory activity against Mycobacterium bovis BCG. Among the derivatives, compound Ib proved to be the most potent derivatives with MIC value of 31.25 microg/mL. Given the fact that 4-amino-1, 2, 4-triazole-5-thiones Ia-f were the most active derivatives, it could be suggested that this group of derivatives have the potential to be considered as lead compounds for future optimization efforts

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