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
来源：
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS | 2012年 / 22卷 / 17期
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
  • [31] Synthesis of Novel Compounds as New Potent Tyrosinase Inhibitors
    Hamidian, Hooshang
    BIOMED RESEARCH INTERNATIONAL, 2013, 2013
  • [32] Synthesis, molecular docking and molecular dynamics studies of novel tacrine-carbamate derivatives as potent cholinesterase inhibitors
    Ozten, Ozge
    Kurt, Belma Zengin
    Sonmez, Fatih
    Dogan, Berna
    Durdagi, Serdar
    BIOORGANIC CHEMISTRY, 2021, 115
  • [33] Synthesis of novel azo-resveratrol, azo-oxyresveratrol and their derivatives as potent tyrosinase inhibitors
    Song, Yu Min
    Ha, Young Mi
    Kim, Jin-Ah
    Chung, Ki Wung
    Uehara, Yohei
    Lee, Kyung Jin
    Chun, Pusoon
    Byun, Youngjoo
    Chung, Hae Young
    Moon, Hyung Ryong
    BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2012, 22 (24) : 7451 - 7455
  • [34] Cinnamic acid derivatives linked to arylpiperazines as novel potent inhibitors of tyrosinase activity and melanin synthesis
    Romagnoli, Romeo
    Oliva, Paola
    Prencipe, Filippo
    Manfredini, Stefano
    Ricci, Federico
    Corallo, Diana
    Aveic, Sanja
    Mariotto, Elena
    Viola, Giampietro
    Bortolozzi, Roberta
    Germano, Maria Paola
    De Luca, Laura
    EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2022, 231
  • [35] Design, synthesis, and biological evaluation of symmetrical azine derivatives as novel tyrosinase inhibitors
    Karimian, Somaye
    Kazemi, Fatemeh
    Attarroshan, Mahshid
    Gholampour, Maryam
    Hemmati, Shiva
    Sakhteman, Amirhossein
    Behzadipour, Yasaman
    Kabiri, Maryam
    Iraji, Aida
    Khoshneviszadeh, Mehdi
    BMC CHEMISTRY, 2021, 15 (01)
  • [36] Design, synthesis, and biological evaluation of symmetrical azine derivatives as novel tyrosinase inhibitors
    Somaye Karimian
    Fatemeh Kazemi
    Mahshid Attarroshan
    Maryam Gholampour
    Shiva Hemmati
    Amirhossein Sakhteman
    Yasaman Behzadipour
    Maryam Kabiri
    Aida Iraji
    Mehdi Khoshneviszadeh
    BMC Chemistry, 15
  • [37] Synthesis, in vitro inhibitor screening, structure–activity relationship, and molecular dynamic simulation studies of novel thioquinoline derivatives as potent α-glucosidase inhibitors
    RasaDokht Forozan
    Minoo Khalili Ghomi
    Aida Iraji
    Mohammad Nazari Montazer
    Milad Noori
    Navid Dastyafteh
    Somayeh Mojtabavi
    Mohammad Ali Faramarzi
    Seyed Esmaeil Sadat-Ebrahimi
    Bagher Larijani
    Shahrzad Javanshir
    Mohammad Mahdavi
    Scientific Reports, 13
  • [38] Synthesis, kinetic mechanism and docking studies of vanillin derivatives as inhibitors of mushroom tyrosinase
    Ashraf, Zaman
    Rafiq, Muhammad
    Seo, Sung-Yum
    Babar, Mustafeez Mujtaba
    Zaidi, Najam-us-Sahar Sadaf
    BIOORGANIC & MEDICINAL CHEMISTRY, 2015, 23 (17) : 5870 - 5880
  • [39] Design, synthesis and evaluation of cinnamic acid ester derivatives as mushroom tyrosinase inhibitors
    Sheng, Zhaojun
    Ge, Siyuan
    Xu, Ximing
    Zhang, Yan
    Wu, Panpan
    Zhang, Kun
    Xu, Xuetao
    Li, Chen
    Zhao, Denggao
    Tang, Xiaowen
    MEDCHEMCOMM, 2018, 9 (05) : 853 - 861
  • [40] Exploration of Novel Human Tyrosinase Inhibitors by Molecular Modeling, Docking and Simulation Studies
    Mubashir Hassan
    Zaman Ashraf
    Qamar Abbas
    Hussain Raza
    Sung-Yum Seo
    Interdisciplinary Sciences: Computational Life Sciences, 2018, 10 : 68 - 80
12345