Synthesis and Biological Evaluation of Thiosemicarbazide Derivatives Endowed with High Activity toward Mycobacterium Bovis

Document Type: Research article

Authors

1 Pasteur Institute

2 Drug Design and Bioinformatics Unit, Medical Biotechnology Department, Biotechnoloogy Research Center, Pasteur Institute of Iran, Tehran, Iran.

3 Department of Life Science Engineering, Faculty of New Sciences & Technologies, University of Tehran, Tehran, Iran

4 Drug Design and Bioinformatics Unit, Medical Biotechnology Department, Biotechnoloogy Research Center, Pasteur Institute of Iran, Tehran, Iran. Faculty of Chemistry, Kharazmi University, Tehran, Iran

5 Faculty of Chemistry, Kharazmi University, Tehran, Iran

Abstract

Thiosemicarbazides are potent intermediates for the synthesis of pharmaceutical and bioactive materials and thus, they are used extensively in the field of medicinal chemistry. The imine bond (-N=CH-) in these compounds are useful in organic synthesis, in particular for the preparation of heterocycles and non-natural β-aminoacids.In this paper the synthesis of some new thiosemicarbazide derivatives by condensation reaction of various aldehydes or ketones with 4-phenylthiosemicarbazide or thiosemicarbazide is reported. This synthesis method has the advantages of high yields and good bioactivity. The structures of these compounds were confirmed by IR, Mass, 1H NMR, 13C NMR, and single-crystal X-ray diffraction studies. All of these compounds were tested for their in vitro anti-mycobacterial activity. The influence of the functional group and position of substituent on anti-bacterial activity of compounds is investigated too. The preliminary results indicated that all the tested compounds showed good activity against the test organism. The compounds 11 and 30 showed the highest anti-tubercular activity (0.39 μg/mL).

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