Synthesis of Novel and Highly Functionalized 4-hydroxycoumarin Chalcone and their Pyrazoline Derivatives as Anti-Tuberculosis Agents

Author(s): Mohammad Asad, Farzana Beevi, Suresh Pandian Ganesan, Chuan-Wei Oo, Raju Suresh Kumar, Venu Laxmipathi, Hasnah Osman, Mohamed Ashraf Ali

Journal Name: Letters in Drug Design & Discovery

Volume 11 , Issue 2 , 2014

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Condensation of ketones 1a-b with deferent aldehydes 2a-e gives chalcones 3a-j. These chalcones on cyclization with hydrazine hydrate/ phenylhydrazine in the presence of glacial acetic acid give the corresponding pyrazolines 4a-t. The structures of new compounds have been established by extensive IR, NMR and X-ray crystallographic studies and were assayed for their antitubercular activity against M. tuberculosis H37Rv and INH resistant M. tuberculosis strains using agar dilution method. Among the both derivative compounds, 4-hydroxy-3-(5-(4- trifluoromethyl)phenyl)-4,5-dihydro-1H-pyrazol-3-yl-2H-chromen-2-one 4m produced the highest efficacy, exhibited >90% inhibition against MTB at a concentration of 4.94 µM and against INHR-MTB at 14.78 µM.

Keywords: Mycobacterium tuberculosis, 3-Acetyl-4-hydroxycoumarins, Chalcones and Pyrazolines.

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Article Details

Year: 2014
Published on: 27 December, 2013
Page: [222 - 230]
Pages: 9
DOI: 10.2174/15701808113109990055
Price: $65

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