Design and synthesis of 3,5-diaryl-4,5-dihydro-1H-pyrazoles as new tyrosinase inhibitors

被引：31

作者：

Zhou, Zhixuan ^{[1
]}

Zhuo, Jiaru ^{[1
]}

Yan, Sujun ^{[1
]}

Ma, Lin ^{[1
]}

机构：

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

来源：

BIOORGANIC & MEDICINAL CHEMISTRY | 2013年 / 21卷 / 07期

基金：

中国国家自然科学基金;

关键词：

4,5-Dihydro-1H-pyrazole; Mushroom tyrosinase; Inhibit; DERIVATIVES;

D O I：

10.1016/j.bmc.2012.12.054

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 this study, twenty 3,5-diaryl-4,5-dihydro-1H-pyrazole derivatives with hydroxyl(s) (1a-1p, 2a-2d) were synthesized and their inhibitory activity on mushroom tyrosinase was examined. The results showed that among these compounds, 1-(5-(3,4-dihydroxyphenyl)-3-(4-hydroxyphenyl)-4,5-dihydro-1H-pyrazol-1-yl)ethanone 1d was found to be the most potent tyrosinase inhibitor with IC50 value of 0.301 mu M. Kinetic study revealed that these compounds were competitive inhibitors of tyrosinase and their structure-activity relationships were investigated in this article. (C) 2013 Published by Elsevier Ltd.

引用

页码：2156 / 2162

页数：7

共 50 条

[31] Design, synthesis, biological evaluation of 3,5-diaryl-4,5-dihydro-1H-pyrazole carbaldehydes as non-purine xanthine oxidase inhibitors: Tracing the anticancer mechanism via xanthine oxidase inhibition
Joshi, Gaurav
Sharma, Manisha
Kalra, Sourav
Gavande, Navnath S.
Singh, Sandeep
Kumar, Raj
BIOORGANIC CHEMISTRY, 2021, 107
[32] Antipyretic and antioxidant activities of 5-trifluoromethyl-4,5-dihydro-1H-pyrazoles in rats
Pasin, J. S. M.
Ferreira, A. P. O.
Saraiva, A. L. L.
Ratzlaff, V.
Andrighetto, R.
Machado, P.
Marchesan, S.
Zanette, R. A.
Bonacorso, H. G.
Zanatta, N.
Martins, M. A. P.
Ferreira, J.
Mello, C. F.
BRAZILIAN JOURNAL OF MEDICAL AND BIOLOGICAL RESEARCH, 2010, 43 (12) : 1193 - 1202
[33] Activity of 4,5-dihydro-1H-pyrazoles against Mycobacterium tuberculosis and nontuberculous mycobacteria
Ramos, Daniela Fernandes
Fiss, Gabriela
Frizzo, Clarissa Piccinin
Pinto Martins, Marcos Antonio
Bonacorso, Helio Gauze
Zanatta, Nili
Almeida da Silva, Pedro Eduardo
INTERNATIONAL JOURNAL OF ANTIMICROBIAL AGENTS, 2014, 43 (05) : 481 - 483
[34] Targeting Alzheimer's disease with novel dual-function 3,5-diaryl-4,5-dihydro-1H-pyrazole-1-carbothioamide derivatives
Katsogiannou, Aikaterini
Karta, Danai
Di Stefano, Antonio
Oner, Sena
Arslan, Mehmet Enes
Mardinoglu, Adil
Turkez, Hasan
Vassiliou, Stamatia
Cacciatore, Ivana
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY REPORTS, 2024, 12
[35] 1-Acetyl-3,5-diaryl-4,5-dihydro(1H)pyrazoles: Exhibiting Anticancer Activity through Intracellular ROS Scavenging and the Mitochondria-Dependent Death Pathway
Alex, Jimi M.
Singh, Sandeep
Kumar, Raj
ARCHIV DER PHARMAZIE, 2014, 347 (10) : 717 - 727
[36] Dehydrozingerone based 1-acetyl-5-aryl-4,5-dihydro-1H-pyrazoles: Synthesis, characterization and anticancer activity
Ratkovic, Zoran
Muskinja, Jovana
Burmudzija, Adrijana
Rankovic, Branislav
Kosanic, Marijana
Bogdanovic, Goran A.
Markovic, Bojana Simovic
Nikolic, Aleksandar
Arsenijevic, Nebojsa
Dordevic, Snezana
Vukicevic, Rastko D.
JOURNAL OF MOLECULAR STRUCTURE, 2016, 1109 : 82 - 88
[37] Synthesis of 3,5-diaryl-1-pyridoyl pyrazoles
Tayde, VB
Jamode, VS
ASIAN JOURNAL OF CHEMISTRY, 1998, 10 (01) : 187 - 188
[38] A facile and convenient approach to the synthesis of 3,5-diaryl-1H-pyrazoles
Farzad Nikpour
Mahdi Beigvand
Monatshefte für Chemie - Chemical Monthly, 2008, 139
[39] A facile and convenient approach to the synthesis of 3,5-diaryl-1H-pyrazoles
Nikpour, Farzad
Beigvand, Mahdi
MONATSHEFTE FUR CHEMIE, 2008, 139 (07): : 821 - 824
[40] SYNTHESIS AND CHARACTERIZATION OF [(5-MERCAPTO-1,3,4-OXADIAZOL- 2-YL) ARYL]-3,5-DIARYL-4,5-DIHYDRO-1H-PYRAZOLE- 1-CARBOTHIOAMIDES
Ribkovskaia, Zinaida
Pogrebnoi, Serghei
Barba, Alic
Macaev, Fliur
CHEMISTRY JOURNAL OF MOLDOVA, 2011, 6 (01): : 90 - 100

← 1 2 3 4 5 →