Potent acetylcholinesterase inhibitors: Design, synthesis, biological evaluation, and docking study of acridone linked to 1,2,3-triazole derivatives

European Journal of Medicinal Chemistry

Volumn 92, Issue , 2015, Pages 799-806

  Mohammadi Khanaposhtani, Maryam ^a   Saeedi, Mina ^b   Zafarghandi, Narges Shamsaei ^a   Mahdavi, Mohammad ^b   Sabourian, Reyhaneh ^b   Razkenari, Elahe Karimpour ^b   Alinezhad, Heshmatollah ^c   Khanavi, Mahnaz ^b   Foroumadi, Alireza ^b   Shafiee, Abbas ^b   Akbarzadeh, Tahmineh ^a,b  

^a TEHRAN UNIVERSITY OF MEDICAL SCIENCES   (Iran)

^b TEHRAN UNIVERSITY OF MEDICAL SCIENCES   (Iran)

^c UNIVERSITY OF MAZANDARAN   (Iran)

Author keywords

Acetylcholinesterase; Acridone 1,2,3 triazole; Alzheimer's disease; Docking study

Indexed keywords

1,2,3 TRIAZOLE DERIVATIVE; 10 [[1 (4 CHLOROBENZYL) 1H 1,2,3 TRIAZOL 4 YL]METHYL] 2 METHOXYACRIDIN 9(10H) ONE; 10 [[1 (4 CHLOROBENZYL) 1H 1,2,3 TRIAZOL 4 YL]METHYL] 2 METHYLACRIDIN 9(10H) ONE; 10 [[1 (4 CHLOROBENZYL) 1H 1,2,3 TRIAZOL 4 YL]METHYL] 4 FLUOROACRIDIN 9(10H) ONE; 10 [[1 (4 CHLOROBENZYL) 1H 1,2,3 TRIAZOL 4 YL]METHYL] ACRIDIN 9(10H) ONE; 10 [[1 BENZYL 1H 1,2,3 TRIAZOL 4 YL]METHYL] 2 BROMOACRIDIN 9(10H) ONE; 10 [[1 BENZYL 1H 1,2,3 TRIAZOL 4 YL]METHYL] 2 CHLOROACRIDIN 9(10H) ONE; 10 [[1 BENZYL 1H 1,2,3 TRIAZOL 4 YL]METHYL] 2 METHOXYACRIDIN 9(10H) ONE; 10 [[1 BENZYL 1H 1,2,3 TRIAZOL 4 YL]METHYL] 2 METHYLACRIDIN 9(10H) ONE; 10 [[1 BENZYL 1H 1,2,3 TRIAZOL 4 YL]METHYL] 4 FLUOROACRIDIN 9(10H) ONE; 10 [[1 BENZYL 1H 1,2,3 TRIAZOL 4 YL]METHYL]ACRIDIN 9(10H) ONE; 2 BROMO 10 [[1 (4 CHLOROBENZYL) 1H 1,2,3 TRIAZOL 4 YL]METHYL] ACRIDIN 9(10H) ONE; 2 BROMO 10 [[1 (4 NITROBENZYL) 1H 1,2,3 TRIAZOL 4 YL]METHYL] ACRIDIN 9(10H) ONE; 2 CHLORO 10 [[1 (4 CHLOROBENZYL) 1H 1,2,3 TRIAZOL 4 YL]METHYL] ACRIDIN 9(10H) ONE; 2 CHLORO 10 [[1 (4 NITROBENZYL) 1H 1,2,3 TRIAZOL 4 YL]METHYL] ACRIDIN 9(10H) ONE; ACETYLCHOLINESTERASE; ACRIDONE DERIVATIVE; CHOLINESTERASE; CHOLINESTERASE INHIBITOR; RIVASTIGMINE; UNCLASSIFIED DRUG; ACRIDINE DERIVATIVE; ACRIDONE; ANTIOXIDANT; TRIAZOLE DERIVATIVE;

ANTIOXIDANT ACTIVITY; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CONTROLLED STUDY; CYCLIZATION; CYCLOADDITION; DPPH RADICAL SCAVENGING ASSAY; DRUG DESIGN; DRUG SCREENING; DRUG SYNTHESIS; ENZYME INHIBITION; ENZYME INHIBITION ASSAY; HYDROGEN BOND; IN VITRO STUDY; MELTING POINT; MOLECULAR DOCKING; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; ANIMAL; CHEMICAL STRUCTURE; CHEMISTRY; DOSE RESPONSE; ELECTROPHORUS; METABOLISM; MOSQUITO; STRUCTURE ACTIVITY RELATION; SYNTHESIS;

ACETYLCHOLINESTERASE; ACRIDINES; ANIMALS; ANTIOXIDANTS; CHOLINESTERASE INHIBITORS; CULICIDAE; DOSE-RESPONSE RELATIONSHIP, DRUG; DRUG DESIGN; ELECTROPHORUS; MOLECULAR DOCKING SIMULATION; MOLECULAR STRUCTURE; STRUCTURE-ACTIVITY RELATIONSHIP; TRIAZOLES;

EID: 84921902932     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2015.01.044     Document Type: Article

References (33)

1. N.C. Berchtold, C.W. Cotman, Evolution in the conceptualization of dementia and Alzheimer's disease: Greco-Roman period to the 1960s, Neurobiol. Aging 19 (1998) 173-189.
2. C. Ballard, S. Gauthier, A. Corbett, C. Brayne, D. Aarsland, E. Jones, Alzheimer's diseases, Lancet 377 (2011) 1019-1031.
3. C. Mount, C. Downton, Alzheimer disease: progress or profit, Nat. Med. 12 (2006) 780-784.
4. R.E. Becker, N.H. Greig, E. Giacobini, L.S. Schneider, L. Ferrucci, A new roadmap for drug development for Alzheimer's disease, Nat. Rev. Drug Discov. 13 (2014) 156.
5. F. Mao, L. Huang, Z. Luo, A. Liu, C. Lu, Z. Xie, X. Li, O-Hydroxyl-or o-amino benzylamine-tacrine hybrids: multifunctional biometals chelators, antioxidants, and inhibitors of cholinesterase activity and amyloid-b aggregation, Bioorg. Med. Chem. 20 (2012) 5884-5892.
6. X. Zhou, X.-B. Wang, T. Wang, L.-Y. Kong, Design, synthesis, and acetylcholinesterase inhibitory activity of novel coumarin analogues, Bioorg. Med. Chem. 16 (2008) 8011-8021.
7. H. Tang, H.-T. Zhao, S.-M. Zhong, Z.-Y. Wang, Z.-F. Chen, H. Liang, Novel oxoisoaporphine-based inhibitors of acetyl-and butyrylcholinesterase and acetylcholinesterase-induced beta-amyloid aggregation, Bioorg. Med. Chem. Lett. 22 (2012) 2257-2261.
8. M.L. Bolognesi, A. Cavalli, L. Valgimigli, M. Bartolini, M. Rosini, V. Andrisano, M. Recanatini, C. Melchiorre, Multi-target-directed drug design strategy: from a dual binding site acetylcholinesterase inhibitor to a trifunctional compound against Alzheimer's disease, J. Med. Chem. 50 (2007) 6446-6449.
9. Y. Miyamae, M. Kurisu, K. Murakami, J. Han, H. Isoda, K. Irie, H. Shigemori, Protective effects of caffeoylquinic acids on the aggregation and neurotoxicity of the 42-residue amyloid b-protein, Bioorg. Med. Chem. 20 (2012) 5844.
10. E. Scarpini, P. Scheltens, H. Feldman, Treatment of Alzheimer's disease; current status and new perspectives, Lancet Neurol. 2 (2003) 539-547.
11. A. Chatonnet, O. Lockridge, Comparison of butyrylcholinesterase and acetylcholinesterase, Biochem. J. 260 (1989) 625-634.
12. K.A. Carson, C. Geula, M.-M. Mesulam, Electron microscopic localization of cholinesterase activity in Alzheimer brain tissue, Brain Res. 540 (1991) 204-208.
13. L.S. Schneider, A critical review of cholinesterase inhibitors as a treatment modality in Alzheimer's disease, Dialogues Clin. Neurosci. 2 (2000) 111-128.
14. M.-K. Hu, L.-J. Wu, G. Hsiao, M.-H. Yen, Homodimeric tacrine congeners as acetylcholinesterase inhibitors, J. Med. Chem. 45 (2002) 2277-2282.
15. P. Szymanski, M. Markowicz, E. Mikiciuk-Olasik, Synthesis and biological activity of derivatives of tetrahydroacridine as acetylcholinesterase inhibitors, Bioorg. Chem. 39 (2011) 138-142.
16. L. Fang, S. Jumpertz, Y. Zhang, D. Appenroth, C. Fleck, K. Mohr, C. Tränkle, M. Decker, Hybrid molecules from xanomeline and tacrine: enhanced tacrine actions on cholinesterases and muscarinic M1 receptors, J. Med. Chem. 53 (2010) 2094-2103.
17. Y.Y. Yang, W. Yang, W.J. Zuo, Y.B. Zeng, S.B. Liu, W.L. Mei, H.F. Dai, Two new acridone alkaloids from the branch of Atalantia buxifolia and their biological activity, J. Asian Nat. Prod. Res. 15 (2013) 899-904.
18. X.L. Zhu, N.X. Yu, G.F. Hao, W.C. Yang, G.F. Yang, Structural basis of femtomolar inhibitors for acetylcholinesterase subtype selectivity: insights from computational simulations, J. Mol. Graph. Model. 41 (2013) 55-60.
19. W.G. Lewis, L.G. Green, F. Grynszpan, Z. Radic, P.R. Carlier, P. Taylor, M.G. Finn, K.B. Sharpless, Click chemistry in situ: acetylcholinesterase as a reaction vessel for the selective assembly of a femtomolar inhibitor from an array of building blocks, Angew. Chem. Int. Ed. Engl. 41 (2002) 1053-1057.
20. S. Senapati, Y. Cheng, J.A. McCammon, In-situ synthesis of a tacrine-triazolebased inhibitor of acetylcholinesterase: configurational selection imposed by steric interactions, J. Med. Chem. 49 (2006) 6222-6230.
21. H. Akrami, B.F. Mirjalili, M. Khoobi, H. Nadri, A. Moradi, A. Sakhteman, S. Emami, A. Foroumadi, A. Shafiee, Indolinone-based acetylcholinesterase inhibitors: synthesis, biological activity and molecular modeling, Eur. J. Med. Chem. 84 (2014) 375-381.
22. M. Khoobi, M. Alipour, A. Sakhteman, H. Nadri, A. Moradi, M. Ghandi, S. Emami, A. Foroumadi, A. Shafiee, Design, synthesis, biological evaluation and docking study of 5-oxo-4,5-dihydropyrano[3,2-c]chromene derivatives as acetylcholinesterase and butyrylcholinesterase inhibitors, Eur. J. Med. Chem. 68 (2013) 260-269.
23. A. Asadipour, M. Alipour, M. Jafari, M. Khoobi, S. Emami, H. Nadri, A. Sakhteman, A. Moradi, V. Sheibani, F.H. Moghadam, A. Shafiee, A. Foroumadi, Novel coumarin-3-carboxamides bearing N-benzylpiperidine moiety as potent acetylcholinesterase inhibitors, Eur. J. Med. Chem. 70 (2013) 623-630.
24. C. Wolf, S. Liu, X. Mei, A.T. August, M. Casimir, Regioselective copper-catalyzed amination of bromobenzoic acids using aliphatic and aromatic amines, J. Org. Chem. 71 (2006) 3270-3273.
25. R. Hedge, P. Thimmaiah, M.C. Yerigeri, G. Krishnegowda, K.N. Thimmaiah, P.J. Houghton, Anti-calmodulin acridone derivatives modulate vinblastine resistance in multidrug resistant (MDR) cancer cells, Eur. J. Med. Chem. 39 (2004) 161-178.
26. H.C. Kolb, M.G. Finn, K.B. Sharpless, Click chemistry: diverse chemical function from a few good reactions, Angew. Chem. Int. Ed. 40 (2001) 2004-2021.
27. G.L. Ellman, K.D. Courtney, V. Andres Jr., R.M. Feather-Stone, A new and rapid colorimetric determination of acetylcholinesterase activity, Biochem. Pharmacol. 7 (1961) 88-95.
28. B. Kuhn, P. Mohr, M. Stahl, Intramolecular hydrogen bonding in medicinal chemistry, J. Med. Chem. 53 (2010) 2601-2611.
29. C. Bissantz, B. Kuhn, M. Stahl, A medicinal chemist's guide to molecular interactions, J. Med. Chem. 53 (2010) 5061-5084.
30. N. Yassa, H. Razavi Beni, A. Hadjiakhoondi, Free radical scavenging and lipid peroxidation activity of the Shahani black grape, Pak. J. Biol. Sci. 11 (2008) 2513-2516.
31. C.A. Lipinski, F. Lombardo, B.W. Dominy, P.J. Feeney, Experimental and computational approaches to estimate solubility and permeability in drug discovery and development settings, Adv. Drug Deliv. Rev. 23 (1997) 3-25.
32. C.A. Lipinski, Drug-like properties and the causes of poor solubility and poor permeability, J. Pharmacol. Toxicol. Methods 44 (2000) 235-249.
33. ChemOffice, CambridgeSoftCorporation, Cambridge, USA, 2009.