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
  • [21] Novel biphenyl ester derivatives as tyrosinase inhibitors: Synthesis, crystallographic, spectral analysis and molecular docking studies
    Kwong, Huey Chong
    Kumar, C. S. Chidan
    Mah, Siau Hui
    Chia, Tze Shyang
    Quah, Ching Kheng
    Loh, Zi Han
    Chandraju, Siddegowda
    Lim, Gin Keat
    PLOS ONE, 2017, 12 (02):
  • [22] Design, synthesis, in vitro, and in silico evaluations of kojic acid derivatives linked to amino pyridine moiety as potent tyrosinase inhibitors
    Niri, Davood Rezapour
    Sayahi, Mohammad Hosein
    Behrouz, Somayeh
    Moazzam, Ali
    Rasekh, Fatemeh
    Tanideh, Nader
    Irajie, Cambyz
    Nezhad, Mohammad Seif
    Larijani, Bagher
    Iraji, Aida
    Mahdavi, Mohammad
    HELIYON, 2023, 9 (11)
  • [23] Structure-based designing and synthesis of 2-phenylchromone derivatives as potent tyrosinase inhibitors: In vitro and in silico studies
    Ashraf, Jamshaid
    Mughal, Ehsan Ullah
    Alsantali, Reem, I
    Obaid, Rami J.
    Sadiq, Amina
    Naeem, Nafeesa
    Ali, Anser
    Massadaq, Anam
    Javed, Qamar
    Javid, Asif
    Sumrra, Sajjad Hussain
    Zafar, Muhammad Naveed
    Ahmed, Saleh A.
    BIOORGANIC & MEDICINAL CHEMISTRY, 2021, 35
  • [24] Molecular Modelling Studies on Pyrazole Derivatives for the Design of Potent Rearranged during Transfection Kinase Inhibitors
    Bhujbal, Swapnil P.
    Keretsu, Seketoulie
    Cho, Seung Joo
    MOLECULES, 2021, 26 (03):
  • [25] Design, synthesis and molecular modeling of aloe-emodin derivatives as potent xanthine oxidase inhibitors
    Shi, Da-Hua
    Huang, Wei
    Li, Chao
    Liu, Yu-Wei
    Wang, Shi-Fan
    EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2014, 75 : 289 - 296
  • [26] Design, synthesis, and molecular dynamics simulation studies of some novel kojic acid fused 2-amino-3-cyano-4H-pyran derivatives as tyrosinase inhibitors
    Najafi, Zahra
    Haramabadi, Maryam Zandi
    Chehardoli, Gholamabbas
    Ebadi, Ahmad
    Iraji, Aida
    BMC CHEMISTRY, 2024, 18 (01)
  • [27] Design, synthesis, and molecular dynamics simulation studies of some novel kojic acid fused 2-amino-3-cyano-4H-pyran derivatives as tyrosinase inhibitors
    Zahra Najafi
    Maryam Zandi Haramabadi
    Gholamabbas Chehardoli
    Ahmad Ebadi‬
    Aida Iraji
    BMC Chemistry, 18
  • [28] Design, synthesis and evaluation of flavonoid derivatives as potent AChE inhibitors
    Sheng, Rong
    Lin, Xiao
    Zhang, Jing
    Chol, Kim Sun
    Huang, Wenhai
    Yang, Bo
    He, Qiaojun
    Hu, Yongzhou
    BIOORGANIC & MEDICINAL CHEMISTRY, 2009, 17 (18) : 6692 - 6698
  • [29] Design, synthesis, molecular docking and molecular dynamic studies of novel benzimidazole-thiazole derivatives as potent and selective COX-2 inhibitors
    Irmak, Nurdan Ebru
    Saglik, Begum Nurpelin
    Celik, Ismail
    Sen, Hasan Tahsin
    Ozkay, Yusuf
    Ayhan-Kilcigil, Guelgun
    NEW JOURNAL OF CHEMISTRY, 2023, 47 (47) : 21620 - 21632
  • [30] Synthesis and evaluation of bibenzyl glycosides as potent tyrosinase inhibitors
    Tajima, Reiko
    Oozeki, Hiromi
    Muraoka, Seiichi
    Tanaka, Saori
    Motegi, Yukari
    Nihei, Hiroyuki
    Yamada, Yoichi
    Masuoka, Noriyoshi
    Nihei, Ken-ichi
    EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2011, 46 (04) : 1374 - 1381
12345