Molecular Docking, Synthesis, and Tyrosinase Inhibition Activity of Acetophenone Amide: Potential Inhibitor of Melanogenesis

Table 1

The yield, substitution pattern, mushroom tyrosinase inhibition and docking scores of analogues 3(a–e) and 5(a–e).

Compounds	Yield (%)	Substitution pattern		Mushroom tyrosinase inhibition (μM)	Docking score (kcal/mol), PDB ID 2Y9X
		3a	81			3-OH			-2.362
3b	78	4-OH			-4.295
3c	74	2,4-di-OH			-5.564
3d	69	3,4-di-OH			-4.569
3e	76	3,5-di-OH			-3.984
5a	75		-H		-6.173
5b	73		4-OH		-4.264
5c	71		2,4-di-OH		-6.568
5d	78		4-cl		-5.299
5e	72		4-OH	N.d.	-4.628
Arbutin					-4.759
Kojic acid					-3.792

3a: 2-(3-acetylphenylamino)-2-oxoethyl-3-hydroxybenzoate; 3b: 2-(3-acetylphenylamino)-2-oxoethyl-4-hydroxybenzoate; 3c: 2-(3-acetylphenylamino)-2-oxoethyl 2,4-dihydroxybenzoate; 3d: 2-(3-acetylphenylamino)-2-oxoethyl 3,4-dihydroxybenzoate; 3e: 2-(3-acetylphenylamino)-2-oxoethyl 3,5-dihydroxybenzoate; 5a: 2-(3-acetylphenylamino)-2-oxoethylcinnamate; 5b: 2-(3-acetylphenylamino)-2-oxoethyl(E)-3-(4-hydroxyphenyl) acrylate; 5c: 2-(3-acetylphenylamino)-2-oxoethyl(E)-3-(2,4-dihydroxyphenyl)acrylate; 5d: 2-(3-acetylphenyl amino)-2-oxoethyl(E)-3-(4-chlorophenyl)acrylate; 5e: 2-(3-acetylphenylamino)-2-oxoethyl3-(4-hydroxyphenyl) propanoate; SEM: the standard error mean; N.d.: not determined.