Tehran University of Medical Sciences

Science Communicator Platform

Share By
Development of New Coumarin-Piperazine-N-Phenylacetamid Derivatives As Potent Tyrosinase Inhibitors: In Vitro and in Silico Evaluations Publisher



Aghanour Ashtiani MM ; Karimian S ; Iraji A ; Dastyafteh N ; Mohammadikhanaposhtani M ; Larijani B ; Mahdavi M ; Salehi P
Authors

Source: Medicinal Chemistry Research Published:2026


Abstract

Inhibiting tyrosinase is critical for managing pigmentation disorders and preventing enzymatic browning in food and crops. In this research, a series of novel hybrid coumarin- piperazine-N-phenylacetamide derivatives 11a-q were designed and synthesized to inhibit tyrosinase. The structural identification of compounds 11a-q was carried out using spectroscopic methods, including FTIR, 1H-NMR, and 13C-NMR. The inhibitory activity of these compounds against mushroom tyrosinase and their antioxidant properties were evaluated in vitro. All derivatives showed inhibitory effects on tyrosinase at a concentration of 200 µM, and among them, compound 11 L with an IC50 value of 176.65 µM exhibited the highest activity. Also, at this concentration, all compounds showed weak antioxidant activity. In addition, molecular docking and molecular dynamics studies were performed to investigate the type and energy of interactions of compound 11 L with the active site of the active site of the tyrosinase. © The Author(s), under exclusive licence to Springer Science+Business Media, LLC, part of Springer Nature 2026.
Related Docs
View other Related Docs
1. Phthalimide-1,2,3-Triazole Hybrid Compounds As Tyrosinase Inhibitors; Synthesis, Biological Evaluation and Molecular Docking Analysis, Journal of Molecular Structure (2019)
2. Novel Morpholine Containing Cinnamoyl Amides As Potent Tyrosinase Inhibitors, International Journal of Biological Macromolecules (2019)
3. Evaluating the Effects of Disubstituted 3-Hydroxy-1H-Pyrrol-2(5H)-One Analog As Novel Tyrosinase Inhibitors, Bioorganic Chemistry (2022)
Experts (# of related papers)
View all Related Experts
Mohammad Mahdavi (16)
Bagher Larijani (12)
Other Related Docs
4. Design, Synthesis, in Vitro, and in Silico Evaluations of Kojic Acid Derivatives Linked to Amino Pyridine Moiety As Potent Tyrosinase Inhibitors, Heliyon (2023)
5. Design, Synthesis, Biological Evaluation, and Molecular Docking Study of Thioxo-2,3-Dihydroquinazolinone Derivative As Tyrosinase Inhibitors, Journal of Molecular Structure (2022)
6. Benzylidine-N-Phenylhydrazine-1-Carboxamide Derivatives As Tyrosinase Inhibitors: Design, Preparation, Molecular Docking, and Biological Activity, ChemistrySelect (2023)
7. Kinetic Studies, Molecular Docking, and Antioxidant Activity of Novel 1,3-Diphenyl Pyrazole-Thiosemicarbazone With Anti-Tyrosinase and Anti-Melanogenesis Properties, Bioorganic Chemistry (2024)
8. Nitrophenylpiperazine Derivatives As Novel Tyrosinase Inhibitors: Design, Synthesis, and in Silico Evaluations, BMC Chemistry (2024)
9. Synthesis of New Benzimidazole-1,2,3-Triazole Hybrids As Tyrosinase Inhibitors, Chemistry and Biodiversity (2018)
10. New Insights Into the Inhibitory Effect of Phenol Carboxylic Acid Antioxidants on Mushroom Tyrosinase by Molecular Dynamic Studies and Experimental Assessment, Journal of Biomolecular Structure and Dynamics (2023)
11. Design, Synthesis, in Vitro, and in Silico Evaluation of N-Phenylacetamide-Oxindole-Thiosemicarbazide Hybrids As New Potential Tyrosinase Inhibitors, Chemistry and Biodiversity (2022)
12. Design, Synthesis, Enzymatic Inhibition, and Antioxidant Activity of New 4-Phenylpiperazin-Phenoxy-1,2,3-Triazol-Acetamide Derivatives As Tyrosinase Inhibitors, Synlett (2025)
13. A New Insight Into Mushroom Tyrosinase Inhibitors: Docking, Pharmacophore-Based Virtual Screening, and Molecular Modeling Studies, Journal of Biomolecular Structure and Dynamics (2015)
14. The Natural-Based Optimization of Kojic Acid Conjugated to Different Thio-Quinazolinones As Potential Anti-Melanogenesis Agents With Tyrosinase Inhibitory Activity, Bioorganic and Medicinal Chemistry (2021)
15. Rational Design, Synthesis, in Vitro, and in Silico Studies of Chlorophenylquinazolin-4(3H)-One Containing Different Aryl Acetohydrazides As Tyrosinase Inhibitors, Chemistry and Biodiversity (2022)
16. Naturally Occurring and Synthetic Peptides: Efficient Tyrosinase Inhibitors, Journal of Peptide Science (2021)
17. Development of Mercapto-Phenyl-1,2,4-Triazole Bearing Thio-Quinoline As a Novel Class of Tyrosinase Inhibitors: An in Vitro and in Silico Study, Scientific Reports (2025)
18. Anti-Melanogenesis and Anti-Tyrosinase Properties of Aryl-Substituted Acetamides of Phenoxy Methyl Triazole Conjugated With Thiosemicarbazide: Design, Synthesis and Biological Evaluations, Bioorganic Chemistry (2021)
19. Design, Synthesis, and Evaluation of Novel Quinazoline-Benzo[D]Imidazole-Indole Derivatives As Tyrosinase Inhibitors, Results in Chemistry (2026)
20. Synthesis, Biological Evaluation, and Molecular Docking Analysis of Novel 1, 3, 4-Thiadiazole -Based Kojic Acid Derivatives As Tyrosinase Inhibitors, Journal of Molecular Structure (2022)