Rational design, synthesis and structure-activity relationships of 4-alkoxy- and 4-acyloxy-phenylethylenethiosemicarbazone analogues as novel tyrosinase inhibitors

被引：30

作者：

You, Ao ^{[1
]}

Zhou, Jie ^{[1
,2
]}

Song, Senchuan ^{[1
]}

Zhu, Guoxun ^{[1
]}

Song, Huacan ^{[1
]}

Yi, Wei ^{[1
,2
]}

机构：

[1] Sun Yat Sen Univ, Sch Chem & Chem Engn, Guangzhou 510275, Guangdong, Peoples R China

[2] Chinese Acad Sci, Shanghai Inst Mat Med, Ctr Struct & Funct Drug Targets, VARI SIMM Ctr,CAS Key Lab Receptor Res, Shanghai 201203, Peoples R China

来源：

BIOORGANIC & MEDICINAL CHEMISTRY | 2015年 / 23卷 / 05期

关键词：

4-Alkoxy- and 4-acyloxy-phenylethylenethiosemicarbazone analogues; Tyrosinase inhibitor; SARs; Inhibition mechanism; Inhibitory kinetics; MUSHROOM TYROSINASE; BIOLOGICAL EVALUATION; CINNAMIC ACID; DERIVATIVES; PHENYLMETHYLENETHIOSEMICARBAZONES; THIOSEMICARBAZONES; ANTITYROSINASE; STILBENES; KINETICS;

D O I：

10.1016/j.bmc.2015.01.024

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 continuing our program aimed to search for potent compounds as highly efficient tyrosinase inhibitors, here a series of novel 4-alkoxy- and 4-acyloxy-phenylethylenethiosemicarbazone analogues were designed, synthesized and their biological activities on mushroom tyrosinase were evaluated. Notably, most of compounds displayed remarkable tyrosinase inhibitory activities with IC50 value of lower than 1.0 mu M. Furthermore, the structure-activity relationships (SARs) were discussed and the inhibition mechanism and the inhibitory kinetics of selected compounds 7k and 8d were also investigated. Taken together, these results suggested that such compounds could serve as the promising candidates for the treatment of tyrosinase-related disorders and further development of such compounds might be of great interest. (C) 2015 Published by Elsevier Ltd.

引用

页码：924 / 931

页数：8

共 57 条

[31] A novel one-pot synthesis and preliminary biological activity evaluation of cis-restricted polyhydroxy stilbenes incorporating protocatechuic acid and cinnamic acid fragments [J].

Miliovsky, Mitko ;

Svinyarov, Ivan ;

Mitrev, Yavor ;

Evstatieva, Yana ;

Nikolova, Dilyana ;

Chochkova, Maya ;

Bogdanov, Milen G. .

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2013, 66 :185-192

[32]

Namjooyan F, 2011, PLANTA MED, V77, P1389

[33] Chalcones as potent tyrosinase inhibitors: the effect of hydroxyl positions and numbers [J].

Nerya, O ;

Musa, R ;

Khatib, S ;

Tamir, S ;

Vaya, J .

PHYTOCHEMISTRY, 2004, 65 (10) :1389-1395

[34] Analogues of N-hydroxycinnamoylphenalkylamides as inhibitors of human melanocyte-tyrosinase [J].

Okombi, S ;

Rival, D ;

Bonnet, S ;

Mariotte, AM ;

Perrier, E ;

Boumendjel, A .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2006, 16 (08) :2252-2255

[35] The association between Parkinson's disease and melanoma [J].

Pan, Tianhong ;

Li, Xinqun ;

Jankovic, Joseph .

INTERNATIONAL JOURNAL OF CANCER, 2011, 128 (10) :2251-2260

[36] Synthesis of 4′-Thiosemicarbazonegriseofulvin and Its Effects on the Control of Enzymatic Browning and Postharvest Disease of Fruits [J].

Pan, Zhi-Zhen ;

Zhu, Yu-Jing ;

Yu, Xiao-Jie ;

Lin, Qi-Fan ;

Xiao, Rong-Feng ;

Tang, Jian-Yang ;

Chen, Qing-Xi ;

Liu, Bo .

JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 2012, 60 (43) :10784-10788

[37] Tyrosinase: The four oxidation states of the active site and their relevance to enzymatic activation, oxidation and inactivation [J].

Ramsden, Christopher A. ;

Riley, Patrick A. .

BIOORGANIC & MEDICINAL CHEMISTRY, 2014, 22 (08) :2388-2395

[38]

SANCHEZFERRER A, 1995, BBA-PROTEIN STRUCT M, V1247, P1

[39] First Structures of an Active Bacterial Tyrosinase Reveal Copper Plasticity [J].

Sendovski, Mor ;

Kanteev, Margarita ;

Ben-Yosef, Vered Shuster ;

Adir, Noam ;

Fishman, Ayelet .

JOURNAL OF MOLECULAR BIOLOGY, 2011, 405 (01) :227-237

[40] Mushroom tyrosinase: Recent prospects [J].

Seo, SY ;

Sharma, VK ;

Sharma, N .

JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 2003, 51 (10) :2837-2853

← 1 2 3 4 5 6 →