SYNTHESIS AND ANTITUBERCULAR ACTIVITY OF SOME INDANYL THIOSEMICARBAZONE DERIVATIVES

Abstract

Objective: Indanyl derivatives have already drawn some attention as one of the templates or leads for synthesizing compounds of varying biological activities like antimicrobial, analgesic, anti-inflammatory etc. and some thisosemicarbazones have become clinically reputed for their antibacterial and antitubercular activities which are well documented in the literature. In search of newer antitubercular agents, we have planned the synthesis of some indanyl thiosemicarbazone derivatives, namely indan-1-acetic acid-3-thiosemicarbazone (IAT), 6-methoxyindan-1-acetic acid-3-thiosemicarbazone (MIAT), indan-1-acetic acid-3-(p-chlorophenyl) thiosemicarbazone (IACT) and 6-methoxyindan-1-acetic acid-3-(p-chlorophenyl) thiosemicarbazone (MIACT). Our present work reports the synthesis, characterization and antitubercular activities of these compounds.
Materials and methods: Melting points were determined by using the Sunbim melting point apparatus and are uncorrected. The IR spectra were obtained with a Perkin-Elmer 1310 IR spectrophotometer. The 1H NMR and 13C NMR spectra were recorded on JEOL EX (400 MHz) and JEOL EX (100 MHz) spectrophotometer respectively using tetramethylsilane (TMS) as an internal standard. The mass spectra of all compounds were recorded using Hitachi M80B Mass spectrometer. The synthesized compounds were evaluated for in vitro antitubercular activity by Lowenstein-Jensen method.
Results and conclusions: The compounds were characterized by UV, IR, 1H NMR, 13C NMR and MS data. The results of antitubercular activity against some isolated strains of Mycobacterium tuberculosis at the concentration of 100, 200, 300 and 400 mg/ml showed that IAT and IACT were found to be active exhibiting no growth of Mycobacterium tuberculosis after 6-week incubation at 37°C, whereas MIAT and MIACT have been shown to have little or no activity against various strains of this organism.