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Synthesis and antimycobacterial activity of novel 4-[5-(substituted phenyl)-1-phenyl-4,5-dihydro-1H-3-pyrazolyl]-2-methylphenol derivatives

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Abstract

In the present investigation, 4-hydroxy-3-methylacetophenone, on condensation with appropriate aldehydes in methanolic potassium hydroxide solution, yielded the corresponding chalcones (CI-XI). These corresponding chalcones were reacted with phenyl hydrazide in glacial acetic acid, which led to the formation of novel 4-[5-(substituted phenyl)-1-phenyl-4,5-dihydro-1H-3-pyrazolyl]-2-methylphenol derivatives. All newly synthesized compounds were evaluated for their antimycobacterial activities against isoniazid-resistant Mycobacterium tuberculosis using agar dilution. 4-[5-(4-Fluoro phenyl)-1-phenyl-4,5-dihydro-1H-3-pyrazolyl]-2-methylphenol showed good antimycobacterial activity, with a minimum inhibitory concentration of 0.62 μg/ml.

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Acknowledgments

M. Shahar Yar thanks the University Grant Commission-New Delhi, India for a research award. We thank the Tuberculosis Antimicrobial Acquisition and Coordinating Facility (TAACF), National Institute of Allergy and Infections Diseases Southern Research Institute/GW Long Hansen’s Disease Center, Colorado State University Birmingham, AL, for in vitro antimycobacterial screening and Dr. Kiran Smith, National Cancer Institute, Bethesda, MD, for valuable suggestions.

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  1. Faculty of Pharmacy, Jamia Hamdard University, Department of Pharmaceutical Chemistry, Hamdard Nagar, New Delhi, 110062, India

    Mohamed Ashraf Ali & Mohammad Shahar Yar

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  1. Mohamed Ashraf Ali
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  2. Mohammad Shahar Yar
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Correspondence to Mohammad Shahar Yar.

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Ali, M.A., Yar, M.S. Synthesis and antimycobacterial activity of novel 4-[5-(substituted phenyl)-1-phenyl-4,5-dihydro-1H-3-pyrazolyl]-2-methylphenol derivatives. Med Chem Res 15, 463–470 (2007). https://doi.org/10.1007/s00044-007-9000-4

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  • DOI: https://doi.org/10.1007/s00044-007-9000-4

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