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
  • [21] 9H-Carbazole Derivatives Containing the N-Benzyl-1,2,3-triazole Moiety as New Acetylcholinesterase Inhibitors
    Akrami, Hamidreza
    Mirjalili, Bibi F.
    Khoobi, Mehdi
    Moradi, Alireza
    Nadri, Hamid
    Emami, Saeed
    Foroumadi, Alireza
    Vosooghi, Mohsen
    Shafiee, Abbas
    ARCHIV DER PHARMAZIE, 2015, 348 (05) : 366 - 374
  • [22] Synthesis, Biological Activity Evaluation and Molecular Modeling Study on the New Isoconessimine Derivatives as Acetylcholinesterase Inhibitors
    Jin, Guofei
    Yang, Zhongduo
    Xue, Weiwei
    Sheng, Jie
    Shi, Yin
    Yao, Xiaojun
    CHINESE JOURNAL OF CHEMISTRY, 2013, 31 (09) : 1228 - 1233
  • [23] Potent acetylcholinesterase inhibitors: Design, synthesis, biological evaluation, and docking study of acridone linked to 1,2,3-triazole derivatives
    Mohammadi-Khanaposhtani, Maryam
    Saeedi, Mina
    Zafarghandi, Narges Shamsaei
    Mahdavi, Mohammad
    Sabourian, Reyhaneh
    Razkenari, Elahe Karimpour
    Alinezhad, Heshmatollah
    Khanavi, Mahnaz
    Foroumadi, Alireza
    Shafiee, Abbas
    Akbarzadeh, Tahmineh
    EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2015, 92 : 799 - 806
  • [24] Synthesis, biological evaluation and molecular modeling of aloe-emodin derivatives as new acetylcholinesterase inhibitors
    Shi, Da-Hua
    Huang, Wei
    Li, Chao
    Wang, Ling-Ting
    Wang, Shi-Fan
    BIOORGANIC & MEDICINAL CHEMISTRY, 2013, 21 (05) : 1064 - 1073
  • [25] Design, Synthesis, and Evaluation of Novel 2H-Benzo[b][1,4]thiazin-3(4H)-one Derivatives as New Acetylcholinesterase Inhibitors
    Ali, Sazan Haji
    Osmaniye, Derya
    Saglik, Begum Nurpelin
    Levent, Serkan
    Ozkay, Yusuf
    Kaplancikli, Zafer Asim
    MOLECULES, 2022, 27 (07):
  • [26] Synthesis and biological evaluation of benzothiazin-4-ones: a possible new class of acetylcholinesterase inhibitors
    Berwaldt, Gabriele A.
    Gouvea, Daniela P.
    da Silva, Daniel S.
    das Neves, Adriana M.
    Soares, Mayara S. P.
    Azambuja, Juliana H.
    Siqueira, Geonir M.
    Spanevello, Roselia M.
    Cunico, Wilson
    JOURNAL OF ENZYME INHIBITION AND MEDICINAL CHEMISTRY, 2019, 34 (01) : 197 - 203
  • [27] Synthesis, biological evaluation and docking studies of 2,3dihydroquinazolin-4(1H)- one derivatives as inhibitors of cholinesterases
    Sarfraz, Muhammad
    Sultana, Nargis
    Rashid, Umer
    Akram, Muhammad Safwan
    Sadiq, Abdul
    Tariq, Muhammad Ilyas
    BIOORGANIC CHEMISTRY, 2017, 70 : 237 - 244
  • [28] 5,6-Dimethoxybenzofuran-3-one derivatives: a novel series of dual Acetylcholinesterase/Butyrylcholinesterase inhibitors bearing benzyl pyridinium moiety
    Hamid Nadri
    Morteza Pirali-Hamedani
    Alireza Moradi
    Amirhossein Sakhteman
    Alireza Vahidi
    Vahid Sheibani
    Ali Asadipour
    Nouraddin Hosseinzadeh
    Mohammad Abdollahi
    Abbas Shafiee
    Alireza Foroumadi
    DARU Journal of Pharmaceutical Sciences, 21
  • [29] Design, synthesis and cholinesterase inhibitory evaluation study of fluorescent N-benzylpiperidine-4-one derivatives
    Sukumarapillai, Dileep Kumar
    Kooi-Yeong, Khaw
    Kia, Yalda
    Murugaiyah, Vikneswaran
    Iyer, Sathiyanarayanan Kulathu
    MEDICINAL CHEMISTRY RESEARCH, 2016, 25 (08) : 1705 - 1715
  • [30] Synthesis and biological evaluation of 7H-thiazolo[3,2-b]-1,2,4-triazin-7-one derivatives as dual binding site acetylcholinesterase inhibitors
    Liu, Sijie
    Shang, Ruofeng
    Shi, Lanxiang
    Wan, David Chi-Cheong
    Lin, Huangquan
    EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2014, 81 : 237 - 244
12345