Design, synthesis and molecular simulation studies of dihydrostilbene derivatives as potent tyrosinase inhibitors

被引:36
|
作者
Vontzalidou, Argyro [1 ]
Zoidis, Grigoris [1 ,2 ]
Chaita, Eliza [1 ]
Makropoulou, Maria [1 ]
Aligiannis, Nektarios [1 ]
Lambrinidis, George [2 ]
Mikros, Emmanuel [2 ]
Skaltsounis, Alexios-Leandros [1 ]
机构
[1] Univ Athens, Fac Pharm, Dept Pharmacognosy & Nat Prod Chem, GR-15771 Athens, Greece
[2] Univ Athens, Fac Pharm, Dept Pharmaceut Chem, GR-15771 Athens, Greece
关键词
Deoxybenzoins; Dihydrostilbenes; Tyrosinase inhibitors; Kojic acid; Gallic acid; Molecular simulations; IDENTIFICATION; DOPAMINE;
D O I
10.1016/j.bmcl.2012.07.029
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
The synthesis, molecular modeling and biological evaluation of substituted deoxybenzoins and optimized dihydrostilbenes are reported. Preliminary structure-activity relationship data were elucidated and lead compounds suitable for further optimization were discovered. Dihydrostilbene 7 is a particularly potent inhibitor (IC50 = 8.44 mu M, more potent than kojic acid). (C) 2012 Elsevier Ltd. All rights reserved.
引用
收藏
页码:5523 / 5526
页数:4
相关论文
共 50 条
  • [1] Design and synthesis of chalcone derivatives as potent tyrosinase inhibitors and their structural activity relationship
    Akhtar, Muhammad Nadeem
    Sakeh, Nurshafika M.
    Zareen, Seema
    Gul, Sana
    Lo, Kong Mun
    Ul-Haq, Zaheer
    Shah, Syed Adnan Ali
    Ahmad, Syahida
    JOURNAL OF MOLECULAR STRUCTURE, 2015, 1085 : 97 - 103
  • [2] Molecular docking studies of potent inhibitors of tyrosinase and α-glucosidase
    Syed Sikander Azam
    Reaz Uddin
    Adnan Ali Shah Syed
    Medicinal Chemistry Research, 2012, 21 : 1677 - 1683
  • [3] Molecular docking studies of potent inhibitors of tyrosinase and α-glucosidase
    Azam, Syed Sikander
    Uddin, Reaz
    Syed, Adnan Ali Shah
    ul-Haq, Zaheer
    MEDICINAL CHEMISTRY RESEARCH, 2012, 21 (08) : 1677 - 1683
  • [4] Monosubstituted Acetophenone Thiosemicarbazones as Potent Inhibitors of Tyrosinase: Synthesis, Inhibitory Studies, and Molecular Docking
    Haldys, Katarzyna
    Goldeman, Waldemar
    Anger-Gora, Natalia
    Rossowska, Joanna
    Latajka, Rafal
    PHARMACEUTICALS, 2021, 14 (01) : 1 - 17
  • [5] Molecular design of potent tyrosinase inhibitors having the bibenzyl skeleton
    Oozeki, Hiromi
    Tajima, Reiko
    Nihei, Ken-ichi
    BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2008, 18 (19) : 5252 - 5254
  • [6] Design and synthesis of biphenyl derivatives as mushroom tyrosinase inhibitors
    Bao, Kai
    Dai, Yi
    Zhu, Zhi-Bin
    Tu, Feng-Juan
    Zhang, Wei-Ge
    Yao, Xin-Sheng
    BIOORGANIC & MEDICINAL CHEMISTRY, 2010, 18 (18) : 6708 - 6714
  • [7] Carvacrol derivatives as mushroom tyrosinase inhibitors; synthesis, kinetics mechanism and molecular docking studies
    Ashraf, Zaman
    Rafiq, Muhammad
    Nadeem, Humaira
    Hassan, Mubashir
    Afzal, Samina
    Waseem, Muhammad
    Afzal, Khurram
    Latip, Jalifah
    PLOS ONE, 2017, 12 (05):
  • [8] Synthesis and molecular modeling of new 2-benzylidenethiobarbituric acid derivatives as potent tyrosinase inhibitors agents
    Najafi, Zahra
    Kamari-aliabadi, Adel
    Sabourian, Reyhaneh
    Hajimahmoodi, Mannan
    Chehardoli, Gholamabbas
    JOURNAL OF THE CHINESE CHEMICAL SOCIETY, 2022, 69 (04) : 692 - 702
  • [9] Design, synthesis and SAR studies of novel tacrine derivatives as potent cholinesterase inhibitors
    Dogga, Bhushanarao
    Reddy, Eeda Koti
    Sharanya, C. S.
    Abhithaj, J.
    Arun, K. G.
    Kumar, C. S. Ananda
    Rangappa, K. S.
    EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY REPORTS, 2022, 6
  • [10] Design and synthesis of novel hydroxypyridinone derivatives as potential tyrosinase inhibitors
    Zhao, De-Yin
    Zhang, Ming-Xia
    Dong, Xiao-Wu
    Hu, Yong-Zhou
    Dai, Xiao-Yan
    Wei, Xiaoyi
    Hider, Robert C.
    Zhang, Jin-Chao
    Zhou, Tao
    BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2016, 26 (13) : 3103 - 3108