Tehran University of Medical Sciences

Science Communicator Platform

Stay connected! Follow us on X network (Twitter):
Share By
Design and Synthesis of Novel Coumarin-Pyridinium Hybrids: In Vitro Cholinesterase Inhibitory Activity Publisher Pubmed



Vafadarnejad F1 ; Mahdavi M2 ; Karimpourrazkenari E3 ; Edraki N4 ; Sameem B1 ; Khanavi M5 ; Saeedi M3, 6 ; Akbarzadeh T1, 3
Authors

Source: Bioorganic Chemistry Published:2018


Abstract

A novel series of coumarin-pyridinium hybrids were synthesized and evaluated as inhibitors of acetylcholinesterase (AChE) and butyrylcholinesterase (BChE) using Ellman's method. Among synthesized compounds, 1-(3-fluorobenzyl)-4-((2-oxo-2H-chromene-3-carboxamido)methyl)pyridinium bromide (7l) was found to be the most active compound toward AChE (IC50 = 10.14 µM), 1-(3-chlorobenzyl)-3-((2-oxo-2H-chromene-3-carboxamido)methyl)pyridinium bromide (7g) and 1-(2,3-dichlorobenzyl)-3-((2-oxo-2H-chromene-3-carboxamido)methyl)pyridinium chloride (7h) depicted the best BChE inhibitory activity (IC50s = 0.32 and 0.43 µM, respectively). Although most compounds showed moderate to good anti-AChE activity, their anti-BChE activity was more significant and compound 7g was found as the most selective BChE with SI of 101.18. Also, kinetic study of the compounds 7g and 7l displayed a mixed type inhibition for both AChE and BChE. Furthermore, they were evaluated against β-secretase; however, they showed low inhibitory activity. © 2018 Elsevier Inc.
Related Docs
View other Related Docs
1. Design, Synthesis and Anti-Alzheimer's Activity of Novel 1,2,3-Triazole-Chromenone Carboxamide Derivatives, Bioorganic Chemistry (2019)
2. Novel N-Benzylpyridinium Moiety Linked to Arylisoxazole Derivatives As Selective Butyrylcholinesterase Inhibitors: Synthesis, Biological Evaluation, and Docking Study, Bioorganic Chemistry (2019)
3. Synthesis and Biological Activity of Some Benzochromenoquinolinones: Tacrine Analogs As Potent Anti-Alzheimer's Agents, Chemistry and Biodiversity (2019)
Experts (# of related papers)
View all Related Experts
Mohammad Mahdavi (17)
Tahmineh Akbarzadeh (13)
Other Related Docs
4. Synthesis, Docking Study and Neuroprotective Effects of Some Novel Pyrano[3,2-C]Chromene Derivatives Bearing Morpholine/Phenylpiperazine Moiety, Bioorganic and Medicinal Chemistry (2017)
5. Anticholinesterase Activity of Cinnamic Acids Derivatives: In Vitro, in Vivo Biological Evaluation, and Docking Study, Letters in Drug Design and Discovery (2020)
6. Design and Synthesis of Selective Acetylcholinesterase Inhibitors: Arylisoxazole-Phenylpiperazine Derivatives, Chemistry and Biodiversity (2019)
7. 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, Bioorganic Chemistry (2019)
8. Design, Synthesis, and Cholinesterase Inhibition Assay of Coumarin-3-Carboxamide-N-Morpholine Hybrids As New Anti-Alzheimer Agents, Chemistry and Biodiversity (2019)
9. Design, Synthesis, and Evaluation of Novel Cinnamic Acid-Tryptamine Hybrid for Inhibition of Acetylcholinesterase and Butyrylcholinesterase, DARU# Journal of Pharmaceutical Sciences (2020)
10. Design, Synthesis, in Vivo and in Vitro Studies of 1,2,3,4-Tetrahydro-9H-Carbazole Derivatives, Highly Selective and Potent Butyrylcholinesterase Inhibitors, Molecular Diversity (2020)
11. Novel Tetrahydrocarbazole Benzyl Pyridine Hybrids As Potent and Selective Butryl Cholinesterase Inhibitors With Neuroprotective and Β-Secretase Inhibition Activities, European Journal of Medicinal Chemistry (2018)
12. Synthesis and Biological Evaluation of New N-Benzylpyridinium-Based Benzoheterocycles As Potential Anti-Alzheimer's Agents, Bioorganic Chemistry (2019)
13. Design and Synthesis of Novel Arylisoxazole-Chromenone Carboxamides: Investigation of Biological Activities Associated With Alzheimer's Disease, Chemistry and Biodiversity (2020)
14. Design, Synthesis, and Biological Evaluation of Selective and Potent Carbazole-Based Butyrylcholinesterase Inhibitors, Bioorganic and Medicinal Chemistry (2018)
15. Design, Synthesis and Biological Assessment of New 1-Benzyl-4-((4-Oxoquinazolin-3(4H)-Yl)Methyl) Pyridin-1-Ium Derivatives (Bops) As Potential Dual Inhibitors of Acetylcholinesterase and Butyrylcholinesterase, Heliyon (2021)
16. A Review on Tacrine-Based Scaffolds As Multi-Target Drugs (Mtdls) for Alzheimer's Disease, European Journal of Medicinal Chemistry (2017)
17. Novel Tacrine-Coumarin Hybrids Linked to 1,2,3-Triazole As Anti-Alzheimer's Compounds: In Vitro and in Vivo Biological Evaluation and Docking Study, Bioorganic Chemistry (2019)
18. Recent Developments in the Design and Synthesis of Benzylpyridinium Salts: Mimicking Donepezil Hydrochloride in the Treatment of Alzheimer’S Disease, Frontiers in Chemistry (2022)
19. Coumarin Derivatives Bearing Benzoheterocycle Moiety: Synthesis, Cholinesterase Inhibitory, and Docking Simulation Study, Iranian Journal of Basic Medical Sciences (2017)
20. Design, Synthesis, Biological Evaluation, and Docking Study of Acetylcholinesterase Inhibitors: New Acridone-1,2,4-Oxadiazole-1,2,3-Triazole Hybrids, Chemical Biology and Drug Design (2015)