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Synthesis and Antimycobacterial Activity of some Triazole Derivatives–New Route to Functionalized Triazolopyridazines

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 thiocarbohyd...

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Autores principales: Tehrani, Kamaleddin Haj Mohammad Ebrahim, Mashayekhi, Vida, Azerang, Parisa, Minaei, Somayeh, Sardari, Soroush, Kobarfard, Farzad
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Shaheed Beheshti University of Medical Sciences 2015
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4499427/
https://www.ncbi.nlm.nih.gov/pubmed/26185506
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author Tehrani, Kamaleddin Haj Mohammad Ebrahim
Mashayekhi, Vida
Azerang, Parisa
Minaei, Somayeh
Sardari, Soroush
Kobarfard, Farzad
author_facet Tehrani, Kamaleddin Haj Mohammad Ebrahim
Mashayekhi, Vida
Azerang, Parisa
Minaei, Somayeh
Sardari, Soroush
Kobarfard, Farzad
author_sort Tehrani, Kamaleddin Haj Mohammad Ebrahim
collection PubMed
description 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 γ-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 µg/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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spelling pubmed-44994272015-07-16 Synthesis and Antimycobacterial Activity of some Triazole Derivatives–New Route to Functionalized Triazolopyridazines Tehrani, Kamaleddin Haj Mohammad Ebrahim Mashayekhi, Vida Azerang, Parisa Minaei, Somayeh Sardari, Soroush Kobarfard, Farzad Iran J Pharm Res Original Article 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 γ-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 µg/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. Shaheed Beheshti University of Medical Sciences 2015 /pmc/articles/PMC4499427/ /pubmed/26185506 Text en © 2015 by School of Pharmacy, Shaheed Beheshti University of Medical Sciences and Health Services This is an Open Access article distributed under the terms of the Creative Commons Attribution License, (http://creativecommons.org/licenses/by/3.0/) which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.
spellingShingle Original Article
Tehrani, Kamaleddin Haj Mohammad Ebrahim
Mashayekhi, Vida
Azerang, Parisa
Minaei, Somayeh
Sardari, Soroush
Kobarfard, Farzad
Synthesis and Antimycobacterial Activity of some Triazole Derivatives–New Route to Functionalized Triazolopyridazines
title Synthesis and Antimycobacterial Activity of some Triazole Derivatives–New Route to Functionalized Triazolopyridazines
title_full Synthesis and Antimycobacterial Activity of some Triazole Derivatives–New Route to Functionalized Triazolopyridazines
title_fullStr Synthesis and Antimycobacterial Activity of some Triazole Derivatives–New Route to Functionalized Triazolopyridazines
title_full_unstemmed Synthesis and Antimycobacterial Activity of some Triazole Derivatives–New Route to Functionalized Triazolopyridazines
title_short Synthesis and Antimycobacterial Activity of some Triazole Derivatives–New Route to Functionalized Triazolopyridazines
title_sort synthesis and antimycobacterial activity of some triazole derivatives–new route to functionalized triazolopyridazines
topic Original Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4499427/
https://www.ncbi.nlm.nih.gov/pubmed/26185506
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