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Haj Mohammad Ebrahim Tehrani, K., Kobarfard, F., Azerang, P., Mehravar, M., Soleimani, Z., Ghavami, G., Sardari, S. (2013). Synthesis and Antimycobacterial Activity of Symmetric Thiocarbohydrazone Derivatives against Mycobacterium bovis BCG. Iranian Journal of Pharmaceutical Research, 12(2), 331-346. doi: 10.22037/ijpr.2013.1313
Kamaleddin Haj Mohammad Ebrahim Tehrani; Farzad Kobarfard; Parisa Azerang; Maryam Mehravar; Zohreh Soleimani; Ghazaleh Ghavami; Soroush Sardari. "Synthesis and Antimycobacterial Activity of Symmetric Thiocarbohydrazone Derivatives against Mycobacterium bovis BCG". Iranian Journal of Pharmaceutical Research, 12, 2, 2013, 331-346. doi: 10.22037/ijpr.2013.1313
Haj Mohammad Ebrahim Tehrani, K., Kobarfard, F., Azerang, P., Mehravar, M., Soleimani, Z., Ghavami, G., Sardari, S. (2013). 'Synthesis and Antimycobacterial Activity of Symmetric Thiocarbohydrazone Derivatives against Mycobacterium bovis BCG', Iranian Journal of Pharmaceutical Research, 12(2), pp. 331-346. doi: 10.22037/ijpr.2013.1313
Haj Mohammad Ebrahim Tehrani, K., Kobarfard, F., Azerang, P., Mehravar, M., Soleimani, Z., Ghavami, G., Sardari, S. Synthesis and Antimycobacterial Activity of Symmetric Thiocarbohydrazone Derivatives against Mycobacterium bovis BCG. Iranian Journal of Pharmaceutical Research, 2013; 12(2): 331-346. doi: 10.22037/ijpr.2013.1313

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

Article 11, Volume 12, Issue 2, Spring 2013, Page 331-346  XML PDF (692.36 K)
Document Type: Research article
DOI: 10.22037/ijpr.2013.1313
Authors
Kamaleddin Haj Mohammad Ebrahim Tehrani1; Farzad Kobarfardorcid 2; Parisa Azerang3; Maryam Mehravar3; Zohreh Soleimani1; Ghazaleh Ghavami4; Soroush Sardari email orcid 3
1Department of Medicinal Chemistry, School of Pharmacy, Shahid Beheshti University of Medical Sciences, Tehran, Iran.
21- Department of Medicinal Chemistry, School of Pharmacy, Shahid Beheshti University of Medical Sciences, Tehran, Iran. 2- Phytochemistry Research Center, Shahid Beheshti University of Medical Sciences, Tehran, Iran.
3Drug Design and Bioinformatics Unit, Medical Biotechnology Department, Biotechnology Research Center, Tehran, Pasteur Institute, 13164, Iran.
4Drug Design and Bioinformatics Unit, Medical Biotechnology Department, Biotechnology Research Center, Tehran, Pasteur Institute, 13164
Abstract
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.
Keywords
Thiocarbohydrazone; Thiacetazone; Mycobacterium bovis; Antifungal; In silico
Main Subjects
Medicinal chemistry
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