Tehran University of Medical Sciences

Science Communicator Platform

Stay connected! Follow us on X network (Twitter):
Share this content! On (X network) By
Potent Acetylcholinesterase Inhibitors: Design, Synthesis, Biological Evaluation, and Docking Study of Acridone Linked to 1,2,3-Triazole Derivatives Publisher Pubmed



Mohammadikhanaposhtani M1 ; Saeedi M2 ; Zafarghandi NS1 ; Mahdavi M3 ; Sabourian R4 ; Razkenari EK4 ; Alinezhad H5 ; Khanavi M6 ; Foroumadi A3 ; Shafiee A3 ; Akbarzadeh T1, 4
Authors
Show Affiliations
Authors Affiliations
  1. 1. Department of Medicinal Chemistry, Faculty of Pharmacy, Tehran University of Medical Sciences, Tehran, 14176, Iran
  2. 2. Medicinal Plants Research Center, Tehran University of Medical Sciences, Tehran, Iran
  3. 3. Department of Medicinal Chemistry, Faculty of Pharmacy and Pharmaceutical Sciences Research Center, Tehran University of Medical Sciences, Tehran, 14176, Iran
  4. 4. Persian Medicine and Pharmacy Research Center, Tehran University of Medical Sciences, Tehran, Iran
  5. 5. Faculty of Chemistry, University of Mazandaran, Babolsar, Iran
  6. 6. Department of Pharmacognosy, Tehran University of Medical Sciences, Tehran, 14176, Iran

Source: European Journal of Medicinal Chemistry Published:2015


Abstract

A novel series of acridone linked to 1,2,3-triazole derivatives have been synthesized and evaluated in vitro for their acetylcholinesterase (AChE) and butyrylcholinesterase (BChE) inhibitory activities. The synthetic approach was started from the reaction of 2-bromobenzoic acid with aniline derivatives and subsequent cyclization reaction to give acridone derivatives. Then, reaction of the later compounds with propargyl bromide followed by azide-alkyne cycloaddition reaction (click reaction) led to the formation of the title compounds in good yields. Among the synthesized compounds, 10-((1-(4-chlorobenzyl)-1H-1,2,3-triazol-4-yl)methyl)-2-methoxyacridin-9(10H)-one 9g, depicted the most potent anti-AChE activity (IC50 Combining double low line 7.31 μ1/4M). Also, docking study confirmed the results obtained through in vitro experiments and predicted possible binding conformation. © 2015 Elsevier Masson SAS.
Related Docs
View other Related Docs
1. Synthesis of Novel 1,2,3-Triazole-Dihydro[3,2-C[Chromenones As Acetylcholinesterase Inhibitors, Synthetic Communications (2015)
2. 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)
3. Design, Synthesis, Molecular Modeling and Anticholinesterase Activity of Benzylidene-Benzofuran-3-Ones Containing Cyclic Amine Side Chain, Future Medicinal Chemistry (2017)
4. Design, Synthesis and Evaluation of Novel Multi-Target-Directed Ligands for Treatment of Alzheimer's Disease Based on Coumarin and Lipoic Acid Scaffolds, European Journal of Medicinal Chemistry (2018)
5. Cholinesterase Inhibition Activity and Docking Simulation Study of Coumarin Mannich Base Derivatives, Journal of Sciences# Islamic Republic of Iran (2019)
6. Coumarin Derivatives Bearing Benzoheterocycle Moiety: Synthesis, Cholinesterase Inhibitory, and Docking Simulation Study, Iranian Journal of Basic Medical Sciences (2017)
7. 1,2,3-Triazole-Isoxazole Based Acetylcholinesterase Inhibitors: Synthesis, Biological Evaluation and Docking Study, Letters in Drug Design and Discovery (2017)
8. Design and Synthesis of Novel Anti-Alzheimer's Agents: Acridine-Chromenone and Quinoline-Chromenone Hybrids, Bioorganic Chemistry (2016)
Experts (# of related papers)
View all Related Experts
Mohammad Mahdavi (28)
Alireza Foroumadi (22)
Other Related Docs
9. A Review on Tacrine-Based Scaffolds As Multi-Target Drugs (Mtdls) for Alzheimer's Disease, European Journal of Medicinal Chemistry (2017)
10. Synthesis and Biological Evaluation of New N-Benzylpyridinium-Based Benzoheterocycles As Potential Anti-Alzheimer's Agents, Bioorganic Chemistry (2019)
11. Phytochemical Analysis and Evaluation of Biological Activity of Lawsonia Inermis Seeds Related to Alzheimer's Disease, Evidence-based Complementary and Alternative Medicine (2021)
12. Synthesis and Antiacetylcholinesterase Activity Evaluation of New 2-Aryl Benzofuran Derivatives, Letters in Drug Design and Discovery (2016)
13. Design, Synthesis, in Vitro Cytotoxic Activity Evaluation, and Apoptosis-Induction Study of New 9(10H-Acridinone-1,2,3-Triazoles, Molecular Diversity (2015)
14. 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)
15. 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)
16. Design, Synthesis and Anti-Alzheimer's Activity of Novel 1,2,3-Triazole-Chromenone Carboxamide Derivatives, Bioorganic Chemistry (2019)
17. Design, Synthesis, and Cholinesterase Inhibition Assay of Coumarin-3-Carboxamide-N-Morpholine Hybrids As New Anti-Alzheimer Agents, Chemistry and Biodiversity (2019)
18. Aminoalkyl-Substituted Flavonoids: Synthesis, Cholinesterase Inhibition, Β-Amyloid Aggregation, and Neuroprotective Study, Medicinal Chemistry Research (2019)
19. Synthesis and Urease Inhibitory Activity of Some 5-Aminomethylene Barbituric/Thiobarbituric Acid Derivatives, Letters in Drug Design and Discovery (2018)
20. Novel 3-Phenylcoumarin–Lipoic Acid Conjugates As Multi-Functional Agents for Potential Treatment of Alzheimer's Disease, Bioorganic Chemistry (2018)
21. Synthesis, Docking Study, and Biological Evaluation of Novel Umbellipherone/Hymecromone Derivatives As Acetylcholinesterase/Butyrylcholinesterase Inhibitors, Medicinal Chemistry Research (2018)
22. Pyrano[3,2-C]Quinoline Derivatives As New Class of Α-Glucosidase Inhibitors to Treat Type 2 Diabetes: Synthesis, in Vitro Biological Evaluation and Kinetic Study, Medicinal Chemistry (2019)
23. 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)
24. Design and Synthesis of Selective Acetylcholinesterase Inhibitors: Arylisoxazole-Phenylpiperazine Derivatives, Chemistry and Biodiversity (2019)
25. Design, Synthesis, Molecular Docking, and Cholinesterase Inhibitory Potential of Phthalimide-Dithiocarbamate Hybrids As New Agents for Treatment of Alzheimer's Disease, Chemistry and Biodiversity (2019)
26. Novel N,N-Dimethylbarbituric-Pyridinium Derivatives As Potent Urease Inhibitors: Synthesis, in Vitro, and in Silico Studies, Bioorganic Chemistry (2020)
27. 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)
28. Amino-7,8-Dihydro-4H-Chromenone Derivatives As Potential Inhibitors of Acetylcholinesterase and Butyrylcholinesterase for Alzheimer’S Disease Management; in Vitro and in Silico Study, BMC Chemistry (2024)
29. A Qsar Study for the Prediction of Inhibitory Activity of Coumarin Derivatives for the Treatment of Alzheimer’S Disease, Arabian Journal for Science and Engineering (2021)
30. New Imidazo[1,2-A]Pyridin-2-Yl Derivatives As Ache, Bche, and Lox Inhibitors; Design, Synthesis, and Biological Evaluation, Letters in Drug Design and Discovery (2023)
31. Anticholinesterase Activity of Cinnamic Acids Derivatives: In Vitro, in Vivo Biological Evaluation, and Docking Study, Letters in Drug Design and Discovery (2020)
32. 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)
33. Synthesis and Biological Evaluation of 5-Benzylidenerhodanine-3-Acetic Acid Derivatives As Ache and 15-Lox Inhibitors, Journal of Enzyme Inhibition and Medicinal Chemistry (2015)
34. Design and Synthesis of Benzodiazepine-1,2,3-Triazole Hybrid Derivatives As Selective Butyrylcholinesterase Inhibitors, Molecular Diversity (2020)
35. Design and Synthesis of Multi-Target Directed 1,2,3-Triazole-Dimethylaminoacryloyl-Chromenone Derivatives With Potential Use in Alzheimer's Disease, BMC Chemistry (2020)
36. Recent Developments in the Design and Synthesis of Benzylpyridinium Salts: Mimicking Donepezil Hydrochloride in the Treatment of Alzheimer’S Disease, Frontiers in Chemistry (2022)
37. Synthesis of Novel Chromenones Linked to 1,2,3-Triazole Ring System: Investigation of Biological Activities Against Alzheimer's Disease, Bioorganic Chemistry (2017)
38. Novel 3-Aminobenzofuran Derivatives As Multifunctional Agents for the Treatment of Alzheimer’S Disease, Frontiers in Chemistry (2022)
39. 3-Aryl Coumarin Derivatives Bearing Aminoalkoxy Moiety As Multi-Target-Directed Ligands Against Alzheimer's Disease, Chemistry and Biodiversity (2019)
40. Design and Synthesis of Novel Coumarin-Pyridinium Hybrids: In Vitro Cholinesterase Inhibitory Activity, Bioorganic Chemistry (2018)
41. Synthesis and Anticholinergic Activity of 4-Hydroxycoumarin Derivatives Containing Substituted Benzyl-1,2,3-Triazole Moiety, Chemical Biology and Drug Design (2015)
42. Novel Tacrine-1,2,3-Triazole Hybrids: In Vitro, in Vivo Biological Evaluation and Docking Study of Cholinesterase Inhibitors, European Journal of Medicinal Chemistry (2017)
43. 2,4-Dioxochroman Moiety Linked to 1,2,3-Triazole Derivatives As Novel Α-Glucosidase Inhibitors: Synthesis, in Vitro Biological Evaluation, and Docking Study, Current Organic Chemistry (2020)
44. Design, Synthesis, Pharmacological Evaluation, and Docking Study of New Acridone-Based 1,2,4-Oxadiazoles As Potential Anticonvulsant Agents, European Journal of Medicinal Chemistry (2016)