Benzylidine-N-Phenylhydrazine-1-Carboxamide Derivatives As Tyrosinase Inhibitors: Design, Preparation, Molecular Docking, and Biological Activity

Benzylidine-N-Phenylhydrazine-1-Carboxamide Derivatives As Tyrosinase Inhibitors: Design, Preparation, Molecular Docking, and Biological Activity Publisher

Hamedifar H^{1, 2} ; Karimian S³ ; Kabiri M³ ; Bagheri A⁴ ; Zarei M³ ; Moazzam A⁴ ; Mahdavi M⁴ ; Sepehri N^{1, 2} ; Khoshneviszadeh M³

Show Affiliations

1. CinnaGen Medical Biotechnology Research Center, Alborz University of Medical Sciences, Karaj, Iran
2. CinnaGen Research and Production Co., Alborz, Iran
3. Medicinal and Natural Products Chemistry Research Center, Shiraz University of Medical Sciences, Shiraz, Iran
4. Endocrinology and Metabolism Research Center, Endocrinology and Metabolism Clinical Sciences Institute, Tehran University of Medical Sciences, Tehran, Iran

Source: ChemistrySelect Published:2023

Abstract

Ten novel benzylidine-N-phenylhydrazine-1-carboxamide derivatives (7 a–7 j) were synthesized in three steps and evaluated for their tyrosinase inhibitory and antioxidant activities. The spectrophotometric method with L–DOPA as a substrate was used to determine tyrosinase inhibitory activities, and a DPPH assay was used to evaluate antioxidant properties. Among the synthesized compounds, compound 7 c with an ethyl substitution on the C2-N-phenylacetamide ring showed the highest tyrosinase-inhibition activity (IC50=4.36±1.58 μM), which was comparable with that of standard kojic acid (IC50=16.34±1.93 μM). Compounds (7 d) and (7 e) showed potent antioxidant activities (EC50=52.11±4.18 and 92.47±3.32 μM, respectively), which were comparable to those of quercetin. The study of the interactions and binding modes of the tested compounds was accomplished with molecular docking. Docking results corroborated that the active inhibitors were well placed in the mushroom tyrosinase enzyme‘s active site. © 2023 Wiley-VCH GmbH.

Style	Citing Format
MLA	Hamedifar H, et al.. "Benzylidine-N-Phenylhydrazine-1-Carboxamide Derivatives As Tyrosinase Inhibitors: Design, Preparation, Molecular Docking, and Biological Activity." ChemistrySelect, vol. 8, no. 39, 2023, pp. -.
APA	Hamedifar H, Karimian S, Kabiri M, Bagheri A, Zarei M, Moazzam A, Mahdavi M, Sepehri N, Khoshneviszadeh M (2023). Benzylidine-N-Phenylhydrazine-1-Carboxamide Derivatives As Tyrosinase Inhibitors: Design, Preparation, Molecular Docking, and Biological Activity. ChemistrySelect, 8(39), -.
Chicago	Hamedifar H, Karimian S, Kabiri M, Bagheri A, Zarei M, Moazzam A, Mahdavi M, Sepehri N, Khoshneviszadeh M. "Benzylidine-N-Phenylhydrazine-1-Carboxamide Derivatives As Tyrosinase Inhibitors: Design, Preparation, Molecular Docking, and Biological Activity." ChemistrySelect 8, no. 39 (2023): -.
Harvard	Hamedifar H et al. (2023) 'Benzylidine-N-Phenylhydrazine-1-Carboxamide Derivatives As Tyrosinase Inhibitors: Design, Preparation, Molecular Docking, and Biological Activity', ChemistrySelect, 8(39), pp. -.
Vancouver	Hamedifar H, Karimian S, Kabiri M, Bagheri A, Zarei M, Moazzam A, et al.. Benzylidine-N-Phenylhydrazine-1-Carboxamide Derivatives As Tyrosinase Inhibitors: Design, Preparation, Molecular Docking, and Biological Activity. ChemistrySelect. 2023;8(39):-.
BibTex	@article{ author = {Hamedifar H and Karimian S and Kabiri M and Bagheri A and Zarei M and Moazzam A and Mahdavi M and Sepehri N and Khoshneviszadeh M}, title = {Benzylidine-N-Phenylhydrazine-1-Carboxamide Derivatives As Tyrosinase Inhibitors: Design, Preparation, Molecular Docking, and Biological Activity}, journal = {ChemistrySelect}, volume = {8}, number = {39}, pages = {-}, year = {2023} }
RIS	TY - JOUR AU - Hamedifar H AU - Karimian S AU - Kabiri M AU - Bagheri A AU - Zarei M AU - Moazzam A AU - Mahdavi M AU - Sepehri N AU - Khoshneviszadeh M TI - Benzylidine-N-Phenylhydrazine-1-Carboxamide Derivatives As Tyrosinase Inhibitors: Design, Preparation, Molecular Docking, and Biological Activity JO - ChemistrySelect VL - 8 IS - 39 SP - EP - PY - 2023 ER -

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