Synthesis and Evaluation of Chroman-4-One Linked to N-Benzyl Pyridinium Derivatives as New Acetylcholinesterase Inhibitors

被引：22
|
作者：
Arab, Saman [1 ,2 ]
Sadat-Ebrahimi, Seyed-Esmail [1 ,2 ]
Mohammadi-Khanaposhtani, Maryam [1 ,2 ]
Moradi, Alireza [3 ]
Nadri, Hamid [3 ]
Mahdavi, Mohammad [1 ,2 ]
Moghimi, Setareh [1 ,2 ]
Asadi, Mehdi [1 ,2 ]
Firoozpour, Loghman [4 ]
Pirali-Hamedani, Morteza [1 ,2 ]
Shafiee, Abbas [1 ,2 ]
Foroumadi, Alireza [1 ,2 ,4 ]
机构：
[1] Univ Tehran Med Sci, Fac Pharm, Dept Med Chem, Tehran, Iran
[2] Univ Tehran Med Sci, Pharmaceut Sci Res Ctr, Tehran, Iran
[3] Shahid Sadoughi Univ Med Sci, Fac Pharm, Dept Med Chem, Yazd, Iran
[4] Univ Tehran Med Sci, Drug Design & Dev Res Ctr, Tehran, Iran
来源：
ARCHIV DER PHARMAZIE | 2015年 / 348卷 / 09期
关键词：
Acetylcholinesterase; Alzheimer's disease; Chroman-4-one; Docking study; N-Benzyl pyridinium; BETA-AMYLOID AGGREGATION; ALZHEIMERS-DISEASE; ANTICHOLINESTERASE ACTIVITY; BINDING; DESIGN; CHOLINESTERASES; DOCKING; POTENT;
D O I：
10.1002/ardp.201500149
中图分类号：
R914 [药物化学];
学科分类号：
100701 ;
摘要：
A novel series of chroman-4-one derivatives containing the N-benzyl pyridinium moiety were designed, synthesized, and evaluated for their acetylcholinesterase (AChE) inhibitory activities. Among the various synthesized compounds, (E)-1-(2,3-dibromobenzyl)-4-((7-ethoxy-4-oxochroman-3-ylidene)methyl)pyridinium bromide (8l) depicted the most potent anti-AChE activity (IC50=0.048M). In addition, the molecular modeling study allowed us to detect possible binding modes that are in full compliance with the observed results through in vitro experiments.
引用
收藏
页码：643 / 649
页数：7
相关论文
共 50 条
  • [31] New benzyl pyridinium derivatives bearing 2,4-dioxochroman moiety as potent agents for treatment of Alzheimer's disease: Design, synthesis, biological evaluation, and docking study
    Mollazadeh, Marjan
    Mohammadi-Khanaposhtani, Maryam
    Zonouzi, Afsaneh
    Nadri, Hamid
    Najafi, Zahra
    Larijani, Bagher
    Mahdavi, Mohammad
    BIOORGANIC CHEMISTRY, 2019, 87 : 506 - 515
  • [32] Synthesis and Biological Evaluation of 3,6-diaryl-7H-thiazolo[3,2-b] [1,2,4]triazin-7-one Derivatives as Acetylcholinesterase Inhibitors
    Jin, Zhe
    Yang, Liu
    Liu, Si-Jie
    Wang, Jian
    Li, Shuo
    Lin, Huang-Quan
    Wan, David Chi Cheong
    Hu, Chun
    ARCHIVES OF PHARMACAL RESEARCH, 2010, 33 (10) : 1641 - 1649
  • [33] Novel acetylcholinesterase inhibitors: Synthesis, docking and inhibitory activity evaluation of 4-benzamido-N-(1-benzylpiperidin-4-yl) benzamide derivatives
    Mohammadi-Farani, Ahmad
    Nazari, Sara
    Mohammadi, Mahsa
    Navid, Sahar Jamshidy
    Hosseini, Amin
    Aliabadi, Alireza
    RESULTS IN CHEMISTRY, 2024, 7
  • [34] Design, Synthesis, and Assay of New N-acyl-4-(4-aminoalkoxy- phenyl)-thiazole-2-amine Derivatives as Acetylcholinesterase Inhibitors
    Han, Chuang
    Shang, Pan-Pan
    Xu, Yuan
    Wei, Ben-Ben
    Guo, Xin-Yuan
    Jian, Meng-Meng
    Yang, Kan
    Ma, Zheng-Yue
    LETTERS IN DRUG DESIGN & DISCOVERY, 2023, 20 (09) : 1318 - 1328
  • [35] Synthesis, in vitro biological evaluation and molecular modelling of new 2-chloro-3-hydrazinopyrazine derivatives as potent acetylcholinesterase inhibitors on PC12 cells
    Taheri, Maryam
    Aslani, Samira
    Ghafouri, Hossein
    Mohammadi, Asadollah
    Akbary Moghaddam, Vaha
    Moradi, Nastarn
    Naeimi, Hananeh
    BMC CHEMISTRY, 2022, 16 (01)
  • [36] Synthesis of New Indole Derivatives Structurally Related to Donepezil and Their Biological Evaluation as Acetylcholinesterase Inhibitors
    Ismail, Mohamed M.
    Kamel, Mona M.
    Mohamed, Lamia W.
    Faggal, Samar I.
    MOLECULES, 2012, 17 (05): : 4811 - 4823
  • [37] Synthesis of spiro[chroman-2,4′-piperidin]-4-one derivatives as acetyl-CoA carboxylase inhibitors
    Shinde, Pundlik
    Srivastava, Sanjay K.
    Odedara, Rajendra
    Tuli, Davinder
    Munshi, Siralee
    Patel, Jitendra
    Zambad, Shitalkumar P.
    Sonawane, Rajesh
    Gupta, Ramesh C.
    Chauthaiwale, Vijay
    Dutt, Chaitanya
    BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2009, 19 (03) : 949 - 953
  • [38] Design, Synthesis, and Biological Evaluation of 7H-thiazolo[3,2-b]-1,2,4-triazin-7-one Derivatives as Acetylcholinesterase Inhibitors
    Liu, Si-Jie
    Yang, Liu
    Liu, Xiao-Guang
    Luo, Ying
    Cao, Zi-Jian
    Wan, David Chi Cheong
    Lin, Huang-Quan
    Hu, Chun
    LETTERS IN DRUG DESIGN & DISCOVERY, 2010, 7 (01) : 5 - 8
  • [39] Design, Synthesis, and Biological Evaluation of a New Series of Biphenyl/Bibenzyl Derivatives Functioning as Dual Inhibitors of Acetylcholinesterase and Butyrylcholinesterase
    Wang, Dong-mei
    Feng, Bo
    Fu, Hui
    Liu, Ai-lin
    Wang, Lin
    Du, Guan-hua
    Wu, Song
    MOLECULES, 2017, 22 (01):
  • [40] Microwave-assisted one-pot synthesis and antimicrobial evaluation of 2-(1-phenyl-3-(2-thienyl)-1H-pyrazol-4-yl) chroman-4-one derivatives
    Dongamanti, Ashok
    Naji, Hayder Hasan
    Bommidi, Vijaya Lakshmi
    Madderla, Sarasija
    HETEROCYCLIC COMMUNICATIONS, 2016, 22 (05) : 259 - 264
12345