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Synthesis and evaluation of antibacterial and antifungal activities of new (Z)-3-bromo-4-(1,3-diaryl-1H-pyrazol-4-yl)but-3-en-2-ones and 4-(3-methyl-1-phenyl-1H-pyrazol-5-yl)-1,3-diaryl-1H-pyrazoles

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Abstract

Bromination of 4-(1, 3-diaryl-1H-pyrazol-4-yl) but-3-en-2-ones, triggered by a combination of potassium bromide and cerium(IV) ammonium nitrate in a biphasic system consisting of water and dichloromethane furnishes the corresponding monobromo compounds 2 directly, instead of the expected dibromo compounds. The α-bromo compounds 2 were utilized as efficient precursors for the synthesis of several bipyrazolyl derivatives, 4-(3-methyl-1-phenyl-1H-pyrazol-5-yl)-1, 3-diaryl-1H-pyrazoles (3). All the α-bromoenones 2 and bipyrazoles 3 are new compounds and their identity was established by m.p., spectral and analytical data. The new products 2 and 3 were tested for their in vitro antibacterial activity against Staphylococcus aureus, Bacillus subtilis (Gram positive), Escherichia coli, and Pseudomonas aeruginosa (Gram negative) and antifungal activity against Aspergilus flavus and Aspergillus niger. The antimicrobial activity of the tested compounds is compared with the commercially available antibiotic, ciprofloxacin and antifungal agent, fluconazole.

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Acknowledgments

We are thankful to Council of Scientific and Industrial Research (CSIR), New Delhi, India, for the award of senior research fellowship to Sushma to carry out this work.

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Authors and Affiliations

  1. Department of Chemistry, Kurukshetra University, Kurukshetra, 136119, India

    Rashmi Pundeer,  Sushma & Vijay Kiran

  2. Department of Microbiology, Kurukshetra University, Kurukshetra, 136119, India

    Chetan Sharma & K. R. Aneja

  3. Institute of Pharmaceutical Sciences, Kurukshetra University, Kurukshetra, 136119, India

    Om Prakash

Authors
  1. Rashmi Pundeer
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  2. Sushma
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  3. Vijay Kiran
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  4. Chetan Sharma
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  5. K. R. Aneja
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  6. Om Prakash
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Correspondence to Rashmi Pundeer.

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Pundeer, R., Sushma, Kiran, V. et al. Synthesis and evaluation of antibacterial and antifungal activities of new (Z)-3-bromo-4-(1,3-diaryl-1H-pyrazol-4-yl)but-3-en-2-ones and 4-(3-methyl-1-phenyl-1H-pyrazol-5-yl)-1,3-diaryl-1H-pyrazoles. Med Chem Res 22, 4715–4726 (2013). https://doi.org/10.1007/s00044-013-0480-0

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