Synthesis and anticholinesterase activity of coumarin-3-carboxamides bearing tryptamine moiety

被引：100

作者：

Ghanei-Nasab, Samaneh ^{[1
]}

Khoobi, Mehdi ^{[2
,3
,4
,5
]}

Hadizadeh, Farzin ^{[6
]}

Marjani, Azam ^{[1
]}

Moradi, Alireza ^{[7
]}

Nadri, Hamid ^{[7
]}

Emami, Saeed ^{[8
,9
]}

Foroumadi, Alireza ^{[4
,5
]}

Shafiee, Abbas ^{[4
,5
]}

机构：

[1] Islamic Azad Univ, Arak Branch, Dept Chem, Arak, Iran

[2] Univ Tehran Med Sci, Fac Pharm, Dept Pharmaceut Biomat, Tehran, Iran

[3] Univ Tehran Med Sci, Fac Pharm, Med Biomat Res Ctr, Tehran, Iran

[4] Univ Tehran Med Sci, Dept Med Chem, Fac Pharm, Tehran, Iran

[5] Univ Tehran Med Sci, Pharmaceut Sci Res Ctr, Tehran, Iran

[6] Mashhad Univ Med Sci, Sch Pharm, Biotechnol Res Ctr, Mashhad, Iran

[7] Shahid Sadoughi Univ Med Sci, Dept Med Chem, Fac Pharm, Yazd, Iran

[8] Mazandaran Univ Med Sci, Dept Med Chem, Fac Pharm, Sari, Iran

[9] Mazandaran Univ Med Sci, Pharmaceut Sci Res Ctr, Fac Pharm, Sari, Iran

来源：

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY | 2016年 / 121卷

基金：

美国国家科学基金会;

关键词：

Acetylcholinesterase; Butyrylcholinesterase; Alzheimer's disease; Coumarin; Indole; POTENT ACETYLCHOLINESTERASE INHIBITORS; ALZHEIMERS-DISEASE; CHOLINESTERASE-INHIBITORS; BENZYLPYRIDINIUM BROMIDES; CHOLINERGIC HYPOTHESIS; BIOLOGICAL EVALUATION; BETA AGGREGATION; DERIVATIVES; BUTYRYLCHOLINESTERASE; DEMENTIA;

D O I：

10.1016/j.ejmech.2016.05.014

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

A number of N-(2-(1H-indol-3-yl)ethyl)-2-oxo-2H-chromene-3-carboxamides were synthesized and tested against AChE and BuChE. The in vitro assessment of the synthesized compounds 4a-o revealed that most of them had significant activity toward AChE. The SAR study demonstrated that the introduction of benzyloxy moiety on the 7-position of coumarin scaffold can improve the anti-AChE activity. The best result was obtained with 7-(4-fluorobenzyl)oxy moiety in the case of compound 40, displaying IC50 value of 0.16 mu M. Based on the docking study of AChE, the prototype compound 4o was laid across the active site and occupied both peripheral anionic site (PAS) and catalytic anionic site (CAS). (C) 2016 Elsevier Masson SAS. All rights reserved.

引用

页码：40 / 46

页数：7

共 34 条

[1] Synthesis and anti-cholinesterase activity of new 7-hydroxycoumarin derivatives [J].

Alipour, Masoumeh ;

Khoobi, Mehdi ;

Moradi, Alireza ;

Nadri, Hamid ;

Moghadam, Farshad Homayouni ;

Emami, Saeed ;

Hasanpour, Zeinab ;

Foroumadi, Alireza ;

Shafiee, Abbas .

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2014, 82 :536-544

[2] A review on coumarins as acetylcholinesterase inhibitors for Alzheimer's disease [J].

Anand, Preet ;

Singh, Baldev ;

Singh, Nirmal .

BIOORGANIC & MEDICINAL CHEMISTRY, 2012, 20 (03) :1175-1180

[3]

[Anonymous], 2013, GLOBAL OBSERVATORY A

[4] Novel coumarin-3-carboxamides bearing N-benzylpiperidine moiety as potent acetylcholinesterase inhibitors [J].

Asadipour, Ali ;

Alipour, Masoumeh ;

Jafari, Mona ;

Khoobi, Mehdi ;

Emami, Saeed ;

Nadri, Hamid ;

Sakhteman, Amirhossein ;

Moradi, Alireza ;

Sheibani, Vahid ;

Moghadam, Farshad Homayouni ;

Shafiee, Abbas ;

Foroumadi, Alireza .

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2013, 70 :623-630

[5] Synthesis and Anticholinergic Activity of 4-hydroxycoumarin Derivatives Containing Substituted Benzyl-1,2,3-triazole Moiety [J].

Bagheri, Sahar Mohammad ;

Khoobi, Mehdi ;

Nadri, Hamid ;

Moradi, Alireza ;

Emami, Saeed ;

Jalili-Baleh, Leili ;

Jafarpour, Farnaz ;

Moghadam, Farshad Homayouni ;

Foroumadi, Alireza ;

Shafiee, Abbas .

CHEMICAL BIOLOGY & DRUG DESIGN, 2015, 86 (05) :1215-1220

[6] Benzofuran-derived benzylpyridinium bromides as potent acetylcholinesterase inhibitors [J].

Baharloo, Farzaneh ;

Moslemin, Mohammad Hossein ;

Nadri, Hamid ;

Asadipour, Ali ;

Mahdavi, Mohammad ;

Emami, Saeed ;

Firoozpour, Loghman ;

Mohebat, Razieh ;

Shafiee, Abbas ;

Foroumadi, Alireza .

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2015, 93 :196-201

[7] Tau protein isoforms, phosphorylation and role in neurodegenerative disorders [J].

Buée, L ;

Bussière, T ;

Buée-Scherrer, V ;

Delacourte, A ;

Hof, PR .

BRAIN RESEARCH REVIEWS, 2000, 33 (01) :95-130

[8] (-)-Meptazinol-melatonin hybrids as novel dual inhibitors of cholinesterases and amyloid-β aggregation with high antioxidant potency for Alzheimer's therapy [J].

Cheng, Shaobing ;

Zheng, Wei ;

Gong, Ping ;

Zhou, Qiang ;

Xie, Qiong ;

Yu, Lining ;

Zhang, Peiyi ;

Chen, Liangkang ;

Li, Juan ;

Chen, Jianxing ;

Chen, Hailin ;

Chen, Hongzhuan .

BIOORGANIC & MEDICINAL CHEMISTRY, 2015, 23 (13) :3110-3118

[9] Effects of Cholinesterase Inhibitors on the Activities and Protein Levels of Cholinesterases in the Cerebrospinal Fluid of Patients with Alzheimer's Disease: A Review of Recent Clinical Studies [J].

Darreh-Shori, T. ;

Soininen, H. .

CURRENT ALZHEIMER RESEARCH, 2010, 7 (01) :67-73

[10] Neurobiology of butyrylcholinesterase [J].

Darvesh, S ;

Hopkins, DA ;

Geula, C .

NATURE REVIEWS NEUROSCIENCE, 2003, 4 (02) :131-138

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