Design, Synthesis, Enzymatic Inhibition, and Antioxidant Activity of New 4-Phenylpiperazin-Phenoxy-1,2,3-Triazol-Acetamide Derivatives As Tyrosinase Inhibitors

Design, Synthesis, Enzymatic Inhibition, and Antioxidant Activity of New 4-Phenylpiperazin-Phenoxy-1,2,3-Triazol-Acetamide Derivatives As Tyrosinase Inhibitors Publisher

Alaeddini A ; Karimian S ; Noori M ; Dastyafteh N ; Mohammadikhanaposhti M ; Ghomi MK ; Bararjanian M ; Iraji A ; Javanshir S ; Larijani B ; Ranjbar PR ; Mahdavic M

Source: Synlett Published:2025

Abstract

In this study, a 4-phenylpiperazin-phenoxy-1,2,3-triazol-ac-etamide scaffold was designed as a potent skeleton against tyrosinase by molecular hybridization theory. After that, nineteen derivatives of this scaffold were synthesized and evaluated in vitro and in silico against tyrosinase and the obtained data were compared with kojic acid as a strong tyrosinase inhibitor. Among the nineteen synthesized derivatives, four were more potent than kojic acid against mushroom tyrosinase. In this regard, one compound was around twofold more potent than kojic acid and was a competitive inhibitor for tyrosinase. In silico molecular modeling studies of the interactions of it and kojic acid with the active site of tyrosinase showed that this compound has more favorable binding energy than kojic acid. Moreover, a dynamics study of this compound showed that this compound forms a stable complex with tyrosinase. © 2025 Elsevier B.V., All rights reserved.

Style	Citing Format
MLA	Alaeddini A, et al.. "Design, Synthesis, Enzymatic Inhibition, and Antioxidant Activity of New 4-Phenylpiperazin-Phenoxy-1,2,3-Triazol-Acetamide Derivatives As Tyrosinase Inhibitors." Synlett, vol. 36, no. 16, 2025, pp. 2559-2564.
APA	Alaeddini A, Karimian S, Noori M, Dastyafteh N, Mohammadikhanaposhti M, Ghomi MK, Bararjanian M, Iraji A, Javanshir S, Larijani B, Ranjbar PR, Mahdavic M (2025). Design, Synthesis, Enzymatic Inhibition, and Antioxidant Activity of New 4-Phenylpiperazin-Phenoxy-1,2,3-Triazol-Acetamide Derivatives As Tyrosinase Inhibitors. Synlett, 36(16), 2559-2564.
Chicago	Alaeddini A, Karimian S, Noori M, Dastyafteh N, Mohammadikhanaposhti M, Ghomi MK, Bararjanian M, et al.. "Design, Synthesis, Enzymatic Inhibition, and Antioxidant Activity of New 4-Phenylpiperazin-Phenoxy-1,2,3-Triazol-Acetamide Derivatives As Tyrosinase Inhibitors." Synlett 36, no. 16 (2025): 2559-2564.
Harvard	Alaeddini A et al. (2025) 'Design, Synthesis, Enzymatic Inhibition, and Antioxidant Activity of New 4-Phenylpiperazin-Phenoxy-1,2,3-Triazol-Acetamide Derivatives As Tyrosinase Inhibitors', Synlett, 36(16), pp. 2559-2564.
Vancouver	Alaeddini A, Karimian S, Noori M, Dastyafteh N, Mohammadikhanaposhti M, Ghomi MK, et al.. Design, Synthesis, Enzymatic Inhibition, and Antioxidant Activity of New 4-Phenylpiperazin-Phenoxy-1,2,3-Triazol-Acetamide Derivatives As Tyrosinase Inhibitors. Synlett. 2025;36(16):2559-2564.
BibTex	@article{ author = {Alaeddini A and Karimian S and Noori M and Dastyafteh N and Mohammadikhanaposhti M and Ghomi MK and Bararjanian M and Iraji A and Javanshir S and Larijani B and Ranjbar PR and Mahdavic M}, title = {Design, Synthesis, Enzymatic Inhibition, and Antioxidant Activity of New 4-Phenylpiperazin-Phenoxy-1,2,3-Triazol-Acetamide Derivatives As Tyrosinase Inhibitors}, journal = {Synlett}, volume = {36}, number = {16}, pages = {2559-2564}, year = {2025} }
RIS	TY - JOUR AU - Alaeddini A AU - Karimian S AU - Noori M AU - Dastyafteh N AU - Mohammadikhanaposhti M AU - Ghomi MK AU - Bararjanian M AU - Iraji A AU - Javanshir S AU - Larijani B AU - Ranjbar PR AU - Mahdavic M TI - Design, Synthesis, Enzymatic Inhibition, and Antioxidant Activity of New 4-Phenylpiperazin-Phenoxy-1,2,3-Triazol-Acetamide Derivatives As Tyrosinase Inhibitors JO - Synlett VL - 36 IS - 16 SP - 2559 EP - 2564 PY - 2025 ER -

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