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Synthesis, anti-inflammatory and antimicrobial evaluation of novel N1-(quinolin-4yl)ethane-1,2-diamine phenyl urea derivatives

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Abstract

A series of substituted N-(quinolin-4-yl)ethanediamine phenyl urea derivatives of biological interest were prepared by sequential quinoline synthesis, chlorination, and substitution reaction followed by reaction of resulting amine with different aryl isocyanates. All synthesized compounds (1–13) were screened for their pro-inflammatory cytokines (TNF-α and IL-6) and antimicrobial activity (antibacterial and antifungal). Biological activity evaluation study revealed that among all the compounds screened, compounds 4 and 6 were found to have promising anti-inflammatory activity (up to 78–71 % TNF-α and 96–90 % IL-6 inhibitory activity) at a higher concentration of 10 μM with reference to standard dexamethasone (72 % TNF-α and 86 % IL-6 inhibitory activities at 1 μM). Compounds 6, 8, 10, and 11 overall exhibited promising antimicrobial activity at MIC values ranging from 10 to 30 μg/mL against all the selected pathogenic bacteria and fungi.

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Acknowledgments

The authors would like to thank Mr. R.B. Ingle, Department of Microbiology, Shri Shivaji Collage, Akola for biological screening studies of the newly synthesized compounds.

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Authors and Affiliations

  1. Department of Chemistry, Maharashtra Udayagiri Mahavidyalaya, Udgir, 413 517, India

    Ashish P. Keche, Girish D. Hatnapure, Satish S. Birajdar & Vandana M. Kamble

  2. Department of Chemistry, The Institute of Science, Mumbai, 400 032, India

    Vandana M. Kamble

  3. Dendrimer and Bio-organic Chemistry Laboratory, School of Chemical Science, S. R. T. M. University, Nanded, 431 606, India

    Rajesh H. Tale & Atish H. Rodge

Authors
  1. Ashish P. Keche
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  2. Girish D. Hatnapure
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  3. Rajesh H. Tale
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  4. Atish H. Rodge
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  5. Satish S. Birajdar
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  6. Vandana M. Kamble
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Correspondence to Vandana M. Kamble.

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Keche, A.P., Hatnapure, G.D., Tale, R.H. et al. Synthesis, anti-inflammatory and antimicrobial evaluation of novel N1-(quinolin-4yl)ethane-1,2-diamine phenyl urea derivatives. Med Chem Res 22, 1480–1487 (2013). https://doi.org/10.1007/s00044-012-0144-5

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  • DOI: https://doi.org/10.1007/s00044-012-0144-5

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