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Synthesis of 4-N-α-coumaryl amino acids and investigation of their antioxidant, antimicrobial activities and fluorescence spectra

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Abstract

An efficient metal-free approach for the synthesis of N-coumaryl amino acids and the first one-step synthesis of 4-hydrazinocoumarin from 4-hydroxycoumarin was developed. The nucleophilic addition of amino acid methyl esters to 4-tosylcoumarins produced a series of 4-N-α-coumaryl amino acids in good to excellent yields without racemization. The antioxidant activities of the synthesized compounds were investigated using DPPH and FRAP methods. 4-Hydrazinocoumarin and N-coumaryl tyrosine had the best antioxidant activity. The antimicrobial activities of the compounds against Gram-positive was stronger than Gram-negative. 4-Hydrazinocoumarin showed the best antibacterial effect.

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Acknowledgements

This research was supported by National Institute for Medical Research Development (Grant No. 943185).

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Authors and Affiliations

  1. Peptide Chemistry Research Center, K. N. Toosi University of Technology, Tehran, P. O. Box 15875-4416, Iran

    Hajar Golshadi Ghalehshahi & Saeed Balalaie

  2. Medical Biology Research Center, Kermanshah University of Medical Sciences, Kermanshah, Iran

    Saeed Balalaie

  3. Medicinal Plant and Drug Research Institute, Shahid Beheshti University, Tehran, Iran

    Atousa Aliahmadi & Roya Moghimi

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  1. Hajar Golshadi Ghalehshahi
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  2. Saeed Balalaie
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  3. Atousa Aliahmadi
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  4. Roya Moghimi
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Correspondence to Saeed Balalaie.

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Ghalehshahi, H.G., Balalaie, S., Aliahmadi, A. et al. Synthesis of 4-N-α-coumaryl amino acids and investigation of their antioxidant, antimicrobial activities and fluorescence spectra. Amino Acids 50, 1461–1470 (2018). https://doi.org/10.1007/s00726-018-2624-5

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  • DOI: https://doi.org/10.1007/s00726-018-2624-5

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