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Microwave-assisted synthesis, molecular docking and antimicrobial activity of novel 2-(3-aryl,1-phenyl-1H-pyrazol-4-yl)-8H-pyrano[2,3-f]chromen-4-ones

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Abstract

An efficient synthetic protocol of microwave-assisted synthesis of some novel 2-(3-aryl,1-phenyl-1H-pyrazol-4-yl)-8H-pyrano[2,3-f]chromen-4-ones 6a–j in excellent yields starting from 3-(3-aryl,1-phenyl-1H-pyrazol-4-yl)-1-(5-hydroxy-2H-chromen-6-yl)-propenones 5a–j was described. This approach offers the advantages of short reaction time (3–5 min), mild reaction conditions, high yields (80–88 %) and convenient operation. All the synthesized compounds were tested in vitro for their antimicrobial activity. The compounds 5h (Ar = 3-ethoxyphenyl), 6c (Ar = 4-chlorophenyl), 6e (Ar = 4-hydroxyphenyl) and 6i (Ar = 3,4-methoxyphenyl) were found to be potent against tested bacterial strains, and compounds 5g (Ar = 4-ethoxyphenyl), 6c (Ar = 4-chlorophenyl) and 6i (Ar = 3,4-methoxyphenyl) were found to be potent against tested fungal strains. The final compounds were subjected to molecular docking studies for the inhibition of enzyme DNA gyrase. The in silico molecular docking results are matching with the in vitro antimicrobial studies, and they may be considered as good inhibitor of DNA gyrase.

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Acknowledgments

The authors are thankful to the Head, Department of Chemistry, Osmania University, Hyderabad, for providing laboratory facilities and one of the authors Kavitha Rangu, thankful to UGC, New Delhi, India, for financial support. We are also thankful to The Director, CFRD, Osmania University, Hyderabad, for providing elemental and spectral analysis facilities.

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Authors and Affiliations

  1. Green and Medicinal Chemistry Lab, Department of Chemistry, Osmania University, Hyderabad, 500 007, India

    Dongamanti Ashok, Kavitha Rangu, Velagapuri Hanumantha Rao & Srinivas Gundu

  2. Molecular Modeling and Medicinal Chemistry Group, Department of Chemistry, Osmania University, Hyderabad, 500 007, India

    Ballu Srilata & Manga Vijjulatha

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  1. Dongamanti Ashok
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  2. Kavitha Rangu
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  3. Velagapuri Hanumantha Rao
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Correspondence to Dongamanti Ashok.

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Ashok, D., Rangu, K., Hanumantha Rao, V. et al. Microwave-assisted synthesis, molecular docking and antimicrobial activity of novel 2-(3-aryl,1-phenyl-1H-pyrazol-4-yl)-8H-pyrano[2,3-f]chromen-4-ones. Med Chem Res 25, 501–514 (2016). https://doi.org/10.1007/s00044-016-1505-2

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