Synthesis, biological evaluation and molecular docking analysis of vaniline-benzylidenehydrazine hybrids as potent tyrosinase inhibitors

被引：33

作者：

Iraji, Aida ^{[1
]}

Adelpour, Tina ^{[2
]}

Edraki, Najmeh ^{[1
]}

Khoshneviszadeh, Mahsima ^{[1
]}

Miri, Ramin ^{[1
]}

Khoshneviszadeh, Mehdi ^{[1
,2
]}

机构：

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

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

来源：

BMC CHEMISTRY | 2020年 / 14卷 / 01期

关键词：

Anti-tyrosinase agents; Methoxybenzohydrazide; Molecular docking; Structure-based design; Kinetic study; DERIVATIVES;

D O I：

10.1186/s13065-020-00679-1

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

In this work, 11 novel compounds based on vaniline and benzylidenehydrazine structure were synthesized with various substituents on phenyl aromatic ring of the molecule and evaluated as tyrosinase inhibitors. These new derivatives showed significant anti-tyrosinase activities, among which 4i demonstrated to be the most potent compound, with IC50 values of 1.58 mu M. The structure-activity relationship study of the novel constructed analogs was fully discussed. Kinetic study of compound 4i showed uncompetitive inhibition towards tyrosinase. Furthermore, the high potency of 4i was supported theoretically by molecular docking evaluations.

引用

页数：11

共 22 条

[1] ALLIUM-SATIVUM (GARLIC) - A NATURAL ANTIBIOTIC [J].

ADETUMBI, MA ;

LAU, BHS .

MEDICAL HYPOTHESES, 1983, 12 (03) :227-237

[2] Dopamine- or L-DOPA-induced neurotoxicity: The role of dopamine quinone formation and tyrosinase in a model of Parkinson's disease [J].

Asanuma, M ;

Miyazaki, I ;

Ogawa, N .

NEUROTOXICITY RESEARCH, 2003, 5 (03) :165-176

[3] The etiology and molecular genetics of human pigmentation disorders [J].

Baxter, Laura L. ;

Pavan, William J. .

WILEY INTERDISCIPLINARY REVIEWS-DEVELOPMENTAL BIOLOGY, 2013, 2 (03) :379-392

[4] An Updated Review of Tyrosinase Inhibitors [J].

Chang, Te-Sheng .

INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES, 2009, 10 (06) :2440-2475

[5] 2-Imino 2H-chromene and 2-(phenylimino) 2H-chromene 3-aryl carboxamide derivatives as novel cytotoxic agents: synthesis, biological assay, and molecular docking study [J].

Edraki, Najmeh ;

Iraji, Aida ;

Firuzi, Omidreza ;

Fattahi, Yousef ;

Mahdavi, Mohammad ;

Foroumadi, Alireza ;

Khoshneviszadeh, Mehdi ;

Shafiee, Abbas ;

Miri, Ramin .

JOURNAL OF THE IRANIAN CHEMICAL SOCIETY, 2016, 13 (12) :2163-2171

[6] The combination of glycolic acid and hydroquinone or kojic acid for the treatment of melasma and related conditions [J].

Garcia, A ;

Fulton, JE .

DERMATOLOGIC SURGERY, 1996, 22 (05) :443-447

[7] Fungal tyrosinases: new prospects in molecular characteristics, bioengineering and biotechnological applications [J].

Halaouli, S ;

Asther, M ;

Sigoillot, JC ;

Hamdi, M ;

Lomascolo, A .

JOURNAL OF APPLIED MICROBIOLOGY, 2006, 100 (02) :219-232

[8]

Iraji A, 2019, MED CHEM, V15, P1

[9] Synthesis and structure-activity relationship study of multi-target triazine derivatives as innovative candidates for treatment of Alzheimer's disease [J].

Iraji, Aida ;

Firuzi, Omidreza ;

Khoshneviszadeh, Mehdi ;

Nadri, Hamid ;

Edraki, Najmeh ;

Miri, Ramin .

BIOORGANIC CHEMISTRY, 2018, 77 :223-235

[10] Competitive inhibition of mushroom tyrosinase by 4-substituted benzaldehydes [J].

Jiménez, M ;

Chazarra, S ;

Escribano, J ;

Cabanes, J ;

García-Carmona, F .

JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 2001, 49 (08) :4060-4063

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