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Design, synthesis, bioactivity, and computational studies of some morpholine-clubbed coumarinyl acetamide and cinnamide derivatives

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Abstract

The novel derivatives of morpholine-clubbed 3-substituted coumarinyl acetamide and cinnamide derivatives 5a–5j and 6a–6j have been synthesized via various 2-chloro-N-phenyl acetamide and cinnamoyl chloride derivatives, respectively. The required motif has been generated through Vilsmeier–Haack reaction on 4-hydroxycoumarin annelation of morpholine followed by imine formation and subsequently condensation with various 2-chloro-N-phenylacetamide and cinnamoyl chloride to furnish the desired molecule. The synthesized molecules were characterized by various spectroscopic methods viz IR, 1H NMR, 13C NMR. Their antimicrobial activities against various strains of bacteria and fungi have been evaluated, and computational studies have also been performed for all the newly synthesized analogs.

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Acknowledgements

I am very thankful to Prof. N. K. Shah, Head of the chemistry Department, School of sciences, Gujarat University, for giving support and facilities. The authors also express their sincere thanks to the Centre of Excellence, Department of Chemistry, Saurashtra University, Rajkot, for spectral analysis. The authors wish to offer their deep gratitude to Department of Microbiology, School of Sciences, Gujarat University, Ahmedabad, for carrying out the biological screenings. Authors are also thankful to GUJCOST, Ghandhinagar, for financial support.

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Authors and Affiliations

  1. Department of Chemistry, School of Science, Gujarat University, Ahmadabad, Gujarat, 380009, India

    Prakashsingh M. Chauhan & Sandeep N. Thummar

  2. Department of Chemistry, Veer Narmad South Gujarat University, Surat, Gujarat, 395007, India

    Kishor H. Chikhalia

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  1. Prakashsingh M. Chauhan
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  2. Sandeep N. Thummar
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  3. Kishor H. Chikhalia
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Correspondence to Kishor H. Chikhalia.

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Chauhan, P.M., Thummar, S.N. & Chikhalia, K.H. Design, synthesis, bioactivity, and computational studies of some morpholine-clubbed coumarinyl acetamide and cinnamide derivatives. J IRAN CHEM SOC 15, 1261–1277 (2018). https://doi.org/10.1007/s13738-018-1324-0

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