Evaluating the effects of disubstituted 3-hydroxy-1H-pyrrol-2(5H)-one analog as novel tyrosinase inhibitors

被引：21

作者：

Alizadeh, Naiemeh ^{[7
]}

Sayahi, Mohammad Hossein ^{[2
]}

Iraji, Aida ^{[3
,4
]}

Yazzaf, Rozita ^{[1
]}

Moazzam, Ali ^{[1
]}

Mobaraki, Koroush ^{[5
]}

Adib, Mehdi

Attarroshan, Mahshid ^{[6
]}

Larijani, Bagher ^{[1
]}

Rastegar, Hossein ^{[8
]}

Khoshneviszadeh, Mehdi ^{[5
,6
,9
]}

Mahdavi, Mohammad ^{[9
]}

机构：

[1] Univ Tehran Med Sci, Endocrinol & Metab Clin Sci Inst, Endocrinol & Metab Res Ctr, Tehran, Iran

[2] Payam Noor Univ, Dept Chem, Tehran, Iran

[3] Shiraz Univ Med Sci, Stem Cells Technol Res Ctr, Shiraz, Iran

[4] Shiraz Univ Med Sci, Cent Res Lab, Shiraz, Iran

[5] Shiraz Univ Med Sci, Fac Pharm, Dept Med Chem, Shiraz, Iran

[6] Shiraz Univ Med Sci, Med & Nat Prod Chem Res Ctr, Shiraz, Iran

[7] Univ Tehran, Coll Sci, Sch Chem, POB 14155-6455, Tehran, Iran

[8] Iranian Food & Drug Adm, Cosmet Prod Res Ctr, MOHE, Tehran, Iran

[9] Univ Tehran Med Sci, Endocrinol & Metab Clin Sci Inst, Tehran, Iran

来源：

BIOORGANIC CHEMISTRY | 2022年 / 126卷

关键词：

Synthesis; 3-hydroxy-1H-pyrrol-2(5H)-one; Tyrosinase inhibitors; Molecular docking; VITAMIN-C; ANTIOXIDANT ACTIVITY; DERIVATIVES; PYRROLE;

D O I：

10.1016/j.bioorg.2022.105876

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

In the present study, a series of 3-hydroxy-1H-pyrrol-2(5H)-one derivative were rationally designed and synthesized. The structure of targeted compounds was confirmed by IR, H-1 NMR, C-13 NMR, and elemental analysis. Next, all derivatives were evaluated as tyrosinase inhibitors, and among the synthesized derivatives, compound 6a was proved to be the most potent inhibitor with an IC50 value of 6.98 +/- 1.05 mu M. Kinetic study of compound 6a confirmed the mixed type of inhibitory activity towards tyrosinase. Furthermore, the results of the molecular docking study showed that this compound fitted well in the active site of tyrosinase and exhibited interaction with important residues of the binding site.

引用

页数：9

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