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Design and synthesis of coumarin–imidazole hybrid and phenyl-imidazoloacrylates as potent antimicrobial and antiinflammatory agents

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Abstract

An improved one pot, multi-component synthesis of tri- and tetrasubstituted coumarin–imidazole hybrid has been synthesized at C4 position in good to excellent yield. The reaction was performed under various catalysts and optimization condition results obtained are satisfactory. Wherein, trisubstituted coumarin–imidazole hybrid compounds were converted into phenyl-imidazole acrylates. Further, all the newly synthesized compounds were screened for their antimicrobial activity against Gram-positive Bacillus flexus and Gram-negative Pseudomonas spp. bacterial strains and two strains of fungi studies having Scopulariopsis spp. and Aspergillus terreus organisms. Similarly, antiinflammatory activity of all the compounds was screened against MMP-2 and MMP-9. Both antimicrobial and antiinflammatory results are excellent, among all compounds, sodium acrylate compounds are quite promising against microbial strains and matrix metalloproteins (MMPs). All the isolated compounds were characterized by IR, NMR, and mass spectral analysis.

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Acknowledgements

The authors express their appreciation to Karnatak University, Dharwad for necessary facilities and UGC-UPE (KU/Sch/UGC-UPE/2013-14/1107) fellowship and also, grateful to the DST, New Delhi, for the financial support. Authors also thank Dr. V. H. Kulkarni, Principal, S.E.T’s College of Pharmacy, Dharwad for necessary facilities. Authors extend their thanks to Anil H. A for recording some spectral analyses at CSIR-National Chemical Laboratory, Pune.

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Authors and Affiliations

  1. Department of Chemistry, Karnatak University, Dharwad, Karnataka, 580003, India

    Megharaja Holiyachi, S. Samundeeswari, Bahubali M. Chougala, Nirmala S. Naik, Jyoti Madar & Lokesh A. Shastri

  2. Novel Drug Design and Discovery Laboratory, Department of Pharmaceutical Chemistry, S.E.T’s College of Pharmacy, Dharwad, Karnataka, 580002, India

    Shrinivas D. Joshi & Sheshagiri R. Dixit

  3. Dr. Prabhakar Kore Basic Science Research Center, KLE University, Belgaum, Karnataka, 590010, India

    Suneel Dodamani & Sunil Jalalpure

  4. KLE University’s College of Pharmacy, Nehru Nagar, Belgaum, Karnataka, 590010, India

    Sunil Jalalpure

  5. Department of Chemistry, G.S.S. College, Belgaum, Karnataka, 590006, India

    Vinay A. Sunagar

Authors
  1. Megharaja Holiyachi
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  2. S. Samundeeswari
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  3. Bahubali M. Chougala
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  4. Nirmala S. Naik
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  6. Lokesh A. Shastri
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  7. Shrinivas D. Joshi
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  8. Sheshagiri R. Dixit
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Corresponding author

Correspondence to Lokesh A. Shastri.

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Holiyachi, M., Samundeeswari, S., Chougala, B.M. et al. Design and synthesis of coumarin–imidazole hybrid and phenyl-imidazoloacrylates as potent antimicrobial and antiinflammatory agents. Monatsh Chem 149, 595–609 (2018). https://doi.org/10.1007/s00706-017-2079-5

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  • DOI: https://doi.org/10.1007/s00706-017-2079-5

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