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Synthesis of tert-butyl (substituted benzamido)phenylcarbamate derivatives: anti-inflammatory activity and docking studies

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Journal of Chemical Biology

Abstract

A series of new tert-butyl 2-(substituted benzamido) phenylcarbamate (4a–4j) were synthesized by the condensation of tert-butyl 2-amino phenylcarbamate (3) with various substituted carboxylic acid in the presence of EDCI and HOBt as coupling reagent, obtain in excellent yields. The structures of all newly synthesized compounds were characterized spectroscopically and evaluated for in vivo anti-inflammatory activity compared to the standard drug, indomethacin, by using the carrageenan-induced rat paw edema protocol. Most of the compounds exhibited a promising anti-inflammatory activity within 9 to 12 h, the percentage of inhibition values ranging from 54.239 to 39.021%. The results revealed that the compounds 4i and 4a exhibited better or equivalent anti-inflammatory activity with the percentage of inhibition of 54.239 and 54.130%, respectively, which was comparable to standard drug. In addition to experimental results, in silico docking studies was used as a tool to verify and expand the experimental outcomes.

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Acknowledgements

The author, Bhookya Shankar thanks to UGC-BSR, (RFSMS-Award No. 805/chem/2013), NEW Delhi, India for financial support in the form of senior research fellowship (SRF) and we thank Indian institute of chemical technology (IICT), Hyderabad, for providing the facilities of spectral analysis. We also thank to Jeeva life science, IDA Uppal, Hyderabad, Telangana, India for providing facilities of biological activity.

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Authors and Affiliations

  1. Department of Chemistry, University College of Science, Osmania University, Saifabad, Hyderabad, 500004, India

    Shankar Bhookya, Jalapathi Pochampally, Anil Valeru & Vianala Sunitha

  2. MMMC Group, Department of Chemistry, University College of Science, Osmania University, Hyderabad, Telangana, 500007, India

    Saikrishna Balabadra & Vijjulatha Manga

  3. Department of Biochemistry, University College of Science, Osmania University, Hyderabad, Telangana, 500007, India

    Karunakar rao Kudle

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  1. Shankar Bhookya
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  2. Jalapathi Pochampally
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Correspondence to Jalapathi Pochampally.

Electronic supplementary material

1H NMR, 13C NMR, IR, Mass spectra of all newly synthesized compounds was included in supplementary information.

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Bhookya, S., Pochampally, J., Valeru, A. et al. Synthesis of tert-butyl (substituted benzamido)phenylcarbamate derivatives: anti-inflammatory activity and docking studies. J Chem Biol 10, 105–115 (2017). https://doi.org/10.1007/s12154-017-0168-x

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  • DOI: https://doi.org/10.1007/s12154-017-0168-x

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