Synthesis of benzamide derivatives and evaluation of their in vitro and in silico tyrosinase inhibitory activities

Tran Hoai Tu, Nguyen Trung Nhan, Dang Hoang Phu
Author affiliations

Authors

  • Tran Hoai Tu Faculty of Chemistry, University of Science, 227 Nguyen Van Cu street, District 5, Ho Chi Minh City 72711, Viet Nam
  • Nguyen Trung Nhan Faculty of Chemistry, University of Science, 227 Nguyen Van Cu street, District 5, Ho Chi Minh City 72711, Viet Nam
  • Dang Hoang Phu 2Vietnam National University Ho Chi Minh City, Linh Trung Ward, Thu Duc City, Ho Chi Minh City, Viet Nam https://orcid.org/0000-0002-4989-9315

DOI:

https://doi.org/10.15625/2525-2518/18302

Keywords:

benzamide derivatives, tyrosinase inhibitory activity, docking studies

Abstract

In this research, six benzamide derivatives were traditionally synthesized using hydrazine, carbazide, and hydroxylamine derivatives through the pre- or in situ activation of the carboxylic acid functionality. Their chemical structures were identified as N′-phenylbenzohydrazide, N′-(2,4-dinitrophenyl)benzohydrazide, N′-(benzoyloxy)benzamide, N-dibenzoylurea, 2-amino-5-(4-phenyl)-1,3,4-thiadiazole, and benzohydrazide based on the interpretation of NMR spectroscopic data. Among these products, N′-phenylbenzohydrazide and N-(benzoyloxy)benzamide showed potent tyrosinase inhibitory activity with the IC50 values of 10.5 and 2.5 μM, respectively, stronger than that of kojic acid (44.6 μM). Docking studies between oxy-tyrosinase and the two active compounds have been carried out to analyze their binding interactions. Both two active compounds showed negative binding free energy values (S values) and some more interactions than the positive control (kojic acid). This discovery provided evidence for the potent tyrosinase inhibitory activity of these two compounds, making them promising candidates for the development of anti-tyrosinase agents in medicine  and cosmetics.

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Published

16-08-2024

How to Cite

[1]
Tran Hoai Tu, Nguyen Trung Nhan, and Dang Hoang Phu, “Synthesis of benzamide derivatives and evaluation of their in vitro and in silico tyrosinase inhibitory activities”, Vietnam J. Sci. Technol., vol. 62, no. 4, pp. 660–669, Aug. 2024.

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Section

Natural Products