Novel coumarin derivatives bearing N-benzyl pyridinium moiety: Potent and dual binding site acetylcholinesterase inhibitors
A novel series of coumarin derivatives linked to benzyl pyridinium group were achieved as potent and dual binding site acetylcholinesterase inhibitors. A novel series of coumarin derivatives linked to benzyl pyridinium group were synthesized and biologically evaluated as inhibitors of both acetylcho...
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| Published in | Bioorganic & medicinal chemistry Vol. 20; no. 24; pp. 7214 - 7222 |
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| Main Authors | , , , , , , , |
| Format | Journal Article |
| Language | English |
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Elsevier Ltd
15.12.2012
Elsevier |
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| Abstract | A novel series of coumarin derivatives linked to benzyl pyridinium group were achieved as potent and dual binding site acetylcholinesterase inhibitors.
A novel series of coumarin derivatives linked to benzyl pyridinium group were synthesized and biologically evaluated as inhibitors of both acetylcholinesterase (AChE) and butyrylcholinesterase (BuChE). The enzyme inhibitory activity of synthesized compounds was measured using colorimetric Ellman’s method. It was revealed that compounds 3e, 3h, 3l, 3r and 3s have shown higher activity compared with donepezil hydrochloride as standard drug. Most of the compounds in these series had nanomolar range IC50 in which compound 3r (IC50=0.11nM) was the most active compound against acetylcholinesterase enzyme. |
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| AbstractList | A novel series of coumarin derivatives linked to benzyl pyridinium group were synthesized and biologically evaluated as inhibitors of both acetylcholinesterase (AChE) and butyrylcholinesterase (BuChE). The enzyme inhibitory activity of synthesized compounds was measured using colorimetric Ellman’s method. It was revealed that compounds 3e, 3h, 3l, 3r and 3s have shown higher activity compared with donepezil hydrochloride as standard drug. Most of the compounds in these series had nanomolar range IC₅₀ in which compound 3r (IC₅₀=0.11nM) was the most active compound against acetylcholinesterase enzyme. A novel series of coumarin derivatives linked to benzyl pyridinium group were achieved as potent and dual binding site acetylcholinesterase inhibitors. A novel series of coumarin derivatives linked to benzyl pyridinium group were synthesized and biologically evaluated as inhibitors of both acetylcholinesterase (AChE) and butyrylcholinesterase (BuChE). The enzyme inhibitory activity of synthesized compounds was measured using colorimetric Ellman’s method. It was revealed that compounds 3e, 3h, 3l, 3r and 3s have shown higher activity compared with donepezil hydrochloride as standard drug. Most of the compounds in these series had nanomolar range IC50 in which compound 3r (IC50=0.11nM) was the most active compound against acetylcholinesterase enzyme. A novel series of coumarin derivatives linked to benzyl pyridinium group were synthesized and biologically evaluated as inhibitors of both acetylcholinesterase (AChE) and butyrylcholinesterase (BuChE). The enzyme inhibitory activity of synthesized compounds was measured using colorimetric Ellmanas method. It was revealed that compounds 3e, 3h, 3l, 3r and 3s have shown higher activity compared with donepezil hydrochloride as standard drug. Most of the compounds in these series had nanomolar range IC50 in which compound 3r (IC50 = 0.11 nM) was the most active compound against acetylcholinesterase enzyme. A novel series of coumarin derivatives linked to benzyl pyridinium group were synthesized and biologically evaluated as inhibitors of both acetylcholinesterase (AChE) and butyrylcholinesterase (BuChE). The enzyme inhibitory activity of synthesized compounds was measured using colorimetric Ellman's method. It was revealed that compounds 3e, 3h, 3l, 3r and 3s have shown higher activity compared with donepezil hydrochloride as standard drug. Most of the compounds in these series had nanomolar range IC(50) in which compound 3r (IC(50) = 0.11 nM) was the most active compound against acetylcholinesterase enzyme. A novel series of coumarin derivatives linked to benzyl pyridinium group were synthesized and biologically evaluated as inhibitors of both acetylcholinesterase (AChE) and butyrylcholinesterase (BuChE). The enzyme inhibitory activity of synthesized compounds was measured using colorimetric Ellman's method. It was revealed that compounds 3e, 3h, 3l, 3r and 3s have shown higher activity compared with donepezil hydrochloride as standard drug. Most of the compounds in these series had nanomolar range IC50 in which compound 3r (IC50 = 0.11 nM) was the most active compound against acetylcholinesterase enzyme. (C) 2012 Elsevier Ltd. All rights reserved. |
| Author | Moradi, Alireza Ghandi, Mehdi Alipour, Masoumeh Sakhteman, Amirhossein Shafiee, Abbas Foroumadi, Alireza Khoobi, Mehdi Nadri, Hamid |
| Author_xml | – sequence: 1 givenname: Masoumeh surname: Alipour fullname: Alipour, Masoumeh organization: School of Chemistry, University College of Science, University of Tehran, PO Box 14155-6455, Tehran, Iran – sequence: 2 givenname: Mehdi surname: Khoobi fullname: Khoobi, Mehdi organization: Department of Medicinal Chemistry, Faculty of Pharmacy, and Pharmaceutical Sciences Research Center, Tehran University of Medical Sciences, Tehran 14176, Iran – sequence: 3 givenname: Alireza surname: Foroumadi fullname: Foroumadi, Alireza organization: Department of Medicinal Chemistry, Faculty of Pharmacy, and Pharmaceutical Sciences Research Center, Tehran University of Medical Sciences, Tehran 14176, Iran – sequence: 4 givenname: Hamid surname: Nadri fullname: Nadri, Hamid organization: Department of Medicinal Chemistry, Faculty of Pharmacy, Shahid Sadoughi University of Medical Sciences, Yazd 8915173143, Iran – sequence: 5 givenname: Alireza surname: Moradi fullname: Moradi, Alireza organization: Department of Medicinal Chemistry, Faculty of Pharmacy, Shahid Sadoughi University of Medical Sciences, Yazd 8915173143, Iran – sequence: 6 givenname: Amirhossein surname: Sakhteman fullname: Sakhteman, Amirhossein organization: Department of Medicinal Chemistry, Faculty of Pharmacy, Shahid Sadoughi University of Medical Sciences, Yazd 8915173143, Iran – sequence: 7 givenname: Mehdi surname: Ghandi fullname: Ghandi, Mehdi organization: School of Chemistry, University College of Science, University of Tehran, PO Box 14155-6455, Tehran, Iran – sequence: 8 givenname: Abbas surname: Shafiee fullname: Shafiee, Abbas email: ashafiee@ams.ac.ir organization: Department of Medicinal Chemistry, Faculty of Pharmacy, and Pharmaceutical Sciences Research Center, Tehran University of Medical Sciences, Tehran 14176, Iran |
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| Keywords | Benzylpyridinium Ellman’s method Coumarin Actylcholinesterase inhibitor CHOLINERGIC HYPOTHESIS BUTYRYLCHOLINESTERASE DESIGN SERIES Ellman's method ALZHEIMERS-DISEASE BIOLOGICAL EVALUATION Organic cation Enzyme Coumarine derivatives Benzene derivatives Enzyme inhibitor Lactone Esterases Binding site Acetylcholinesterase Carboxylic ester hydrolases Hydrolases Anticholinesterase agent |
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| Snippet | A novel series of coumarin derivatives linked to benzyl pyridinium group were achieved as potent and dual binding site acetylcholinesterase inhibitors.
A novel... A novel series of coumarin derivatives linked to benzyl pyridinium group were synthesized and biologically evaluated as inhibitors of both acetylcholinesterase... |
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| SubjectTerms | Acetylcholinesterase Actylcholinesterase inhibitor Animals Benzylpyridinium Binding Sites Biochemistry & Molecular Biology Biological and medical sciences Chemistry Chemistry, Medicinal Chemistry, Organic Cholinesterase Inhibitors - chemistry Cholinesterase Inhibitors - pharmacology Colorimetry Coumarin Coumarins - chemistry Coumarins - pharmacology donepezil Drugs Electrophorus - metabolism Ellman’s method Enzymes inhibitory concentration 50 Life Sciences & Biomedicine Medical sciences Models, Molecular Pharmacology & Pharmacy Pharmacology. Drug treatments Physical Sciences pyridinium Pyridinium Compounds - chemistry Pyridinium Compounds - pharmacology Science & Technology Structure-Activity Relationship |
| Title | Novel coumarin derivatives bearing N-benzyl pyridinium moiety: Potent and dual binding site acetylcholinesterase inhibitors |
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