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Synthesis and Antimycobacterial Activity of Symmetric Thiocarbohydrazone Derivatives against Mycobacterium bovis BCG

In this work, we reported the synthesis and evaluation of antimycobacterial and antifungal activity of a series of thiocarbohydrazone derivatives which are thiacetazone congeners. The target compounds were synthesized in superior yields by reacting thiocarbohydrazide with different aromatic aldehyde...

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Autores principales: Haj Mohammad Ebrahim Tehrani, Kamaleddin, Kobarfard, Farzad, Azerang, Parisa, Mehravar, Maryam, Soleimani, Zohreh, Ghavami, Ghazaleh, Sardari, Soroush
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Shaheed Beheshti University of Medical Sciences 2013
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3813234/
https://www.ncbi.nlm.nih.gov/pubmed/24250608
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author Haj Mohammad Ebrahim Tehrani, Kamaleddin
Kobarfard, Farzad
Azerang, Parisa
Mehravar, Maryam
Soleimani, Zohreh
Ghavami, Ghazaleh
Sardari, Soroush
author_facet Haj Mohammad Ebrahim Tehrani, Kamaleddin
Kobarfard, Farzad
Azerang, Parisa
Mehravar, Maryam
Soleimani, Zohreh
Ghavami, Ghazaleh
Sardari, Soroush
author_sort Haj Mohammad Ebrahim Tehrani, Kamaleddin
collection PubMed
description In this work, we reported the synthesis and evaluation of antimycobacterial and antifungal activity of a series of thiocarbohydrazone derivatives which are thiacetazone congeners. The target compounds were synthesized in superior yields by reacting thiocarbohydrazide with different aromatic aldehydes and methyl ketones. Compounds 8, 19 and 25 were found to be the most potent derivatives, exhibiting acceptable activity against Mycobacterium bovis BCG compared to thiacetazone and ethambutol as reference substances. Compounds 8, 15 and 25 exhibited the highest activity against Candida albicans. The most active compounds had a completely different aromatic ring system with various electronic, steric and lipophilic natures. This is understandable in light of the fact that carbohydrazone derivatives must undergo a metabolic activation step before exerting their anti-TB activity and different SAR rules govern each one of these two processes.
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spelling pubmed-38132342013-11-18 Synthesis and Antimycobacterial Activity of Symmetric Thiocarbohydrazone Derivatives against Mycobacterium bovis BCG Haj Mohammad Ebrahim Tehrani, Kamaleddin Kobarfard, Farzad Azerang, Parisa Mehravar, Maryam Soleimani, Zohreh Ghavami, Ghazaleh Sardari, Soroush Iran J Pharm Res Original Article In this work, we reported the synthesis and evaluation of antimycobacterial and antifungal activity of a series of thiocarbohydrazone derivatives which are thiacetazone congeners. The target compounds were synthesized in superior yields by reacting thiocarbohydrazide with different aromatic aldehydes and methyl ketones. Compounds 8, 19 and 25 were found to be the most potent derivatives, exhibiting acceptable activity against Mycobacterium bovis BCG compared to thiacetazone and ethambutol as reference substances. Compounds 8, 15 and 25 exhibited the highest activity against Candida albicans. The most active compounds had a completely different aromatic ring system with various electronic, steric and lipophilic natures. This is understandable in light of the fact that carbohydrazone derivatives must undergo a metabolic activation step before exerting their anti-TB activity and different SAR rules govern each one of these two processes. Shaheed Beheshti University of Medical Sciences 2013 /pmc/articles/PMC3813234/ /pubmed/24250608 Text en © 2013 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
Haj Mohammad Ebrahim Tehrani, Kamaleddin
Kobarfard, Farzad
Azerang, Parisa
Mehravar, Maryam
Soleimani, Zohreh
Ghavami, Ghazaleh
Sardari, Soroush
Synthesis and Antimycobacterial Activity of Symmetric Thiocarbohydrazone Derivatives against Mycobacterium bovis BCG
title Synthesis and Antimycobacterial Activity of Symmetric Thiocarbohydrazone Derivatives against Mycobacterium bovis BCG
title_full Synthesis and Antimycobacterial Activity of Symmetric Thiocarbohydrazone Derivatives against Mycobacterium bovis BCG
title_fullStr Synthesis and Antimycobacterial Activity of Symmetric Thiocarbohydrazone Derivatives against Mycobacterium bovis BCG
title_full_unstemmed Synthesis and Antimycobacterial Activity of Symmetric Thiocarbohydrazone Derivatives against Mycobacterium bovis BCG
title_short Synthesis and Antimycobacterial Activity of Symmetric Thiocarbohydrazone Derivatives against Mycobacterium bovis BCG
title_sort synthesis and antimycobacterial activity of symmetric thiocarbohydrazone derivatives against mycobacterium bovis bcg
topic Original Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3813234/
https://www.ncbi.nlm.nih.gov/pubmed/24250608
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