Synthesis of new indole derivatives structurally related to donepezil and their biological evaluation as acetylcholinesterase inhibitors

Molecules

Volumn 17, Issue 5, 2012, Pages 4811-4823

  Ismail, Mohamed M ^a   Kamel, Mona M ^a   Mohamed, Lamia W ^a   Faggal, Samar I ^a  

^a CAIRO UNIVERSITY   (Egypt)

Author keywords

Acetylcholinesterase inhibitors; Alzheimer; Donepezil; Indole; Isatin; Oxindole

Indexed keywords

ACETYLCHOLINESTERASE; CHOLINESTERASE INHIBITOR; DONEPEZIL; INDAN DERIVATIVE; INDOLE DERIVATIVE; NOOTROPIC AGENT; PIPERIDINE DERIVATIVE;

ANIMAL; ARTICLE; BINDING SITE; BRAIN; CHEMICAL STRUCTURE; DRUG EFFECT; ENZYMOLOGY; KINETICS; MALE; METABOLISM; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; RAT; STRUCTURE ACTIVITY RELATION; SYNTHESIS; WISTAR RAT;

ACETYLCHOLINESTERASE; ANIMALS; BINDING SITES; BRAIN; CHOLINESTERASE INHIBITORS; INDANS; INDOLES; KINETICS; MAGNETIC RESONANCE SPECTROSCOPY; MALE; MODELS, MOLECULAR; NOOTROPIC AGENTS; PIPERIDINES; RATS; RATS, WISTAR; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 84861488708     PISSN: None     EISSN: 14203049     Source Type: Journal    
DOI: 10.3390/molecules17054811     Document Type: Article

References (15)

1. Zhang, J.; Zhu, D.; Sheng, R.; Wu, H.; Hu, Y.; Wang, F.; Cai T.; Yang, B.; He, Q. A novel acetylcholinesterase inhibitor, significantly improved chemical-induced learning and memory impairments on rodents and protected PC12 cell from apoptosis induced by hydrogen proxide. Eur. J. Pharmacol. 2009, 613, 1-9.
2. Pákáski, M.; Kálmán, J. interactions between amyloid and cholinergic mechanisms in Alzheimer's disease. Neurochem. Int. 2008, 53, 103-111.
3. Sugimoto, H.; Yamanishi, Y.; Limura, H.; Kawakami, Y. Donepezil HCl (E2020) and other acetylcholinesterase inhibitors. Curr. Med. Chem. 2000, 7, 303-317.
4. Racchi, M.; Azzucchelli, M.A.; Porrello, E.; Lanni, C.; Govoni, S. Acetylcholinester inhibitors: Novel activities of old molecules. Phamacol. Res. 2004, 50, 441-451.
5. Wilkinson, D. Pharmacotherapy of Alzheimer's disease. Psychiatry 2008, 7, 9-14.
6. Williams, B.R.; Nazarians, A.; Gill, M.A. A review of rivastigmine: A reversible cholinesterase inhibitor. Clin. Ther. 2003, 25, 1634-1638.
7. Tong, W.; Collantes, E.R.; Chen, Y.; Welsh, W.J. A comparative molecular field analysis study of N-benzyl piperidines as acetylcholinesterase inhibitors. J. Med. Chem. 1996, 39, 380-387.
8. Choe, Y.S.; Oh, S.; Shim, I.; Naruto, S.; Chi, D.Y.; Kim, S.E.; Lee, K.; Choi, Y.; Kim, B. Synthesis and biological evaluation of 18F labeled 3-(1-benzylpiperidin-4-yl) 1-(1-methyl-1Hindol- 3-yl) propan-1-ones for in vitro maping of acetylcholinesterase. Nucl. Med. Biol. 2000, 27, 263-267.
9. Omran, Z.; Cailly, T.; Lescot, E.; Oliveira Santos, J.S.; Agondanou, J.H.; Lisowski, V.; Fabis, F.; Godard, A.M.; Stiebing, S.; Flem, G.L.; et al. Synthesis and biological evaluation as AChE inhibitors of new indanones and thiaindanones related to donepezil. Eur. J. Med. Chem. 2005, 40, 1222-1245.
10. Mutschler, E.; Winkler, W. Synthesis of 1-,2-,and 3-(aminoacetyl) indoles and 1-(aminoacetyl) indulines. Arch. Pharm. 1978, 311, 248-255.
11. Huntress, E.H.; Bornstein, J. A new synthesis of 2,4-dihydroxy quinoline J. Am. Chem. Soc. 1949, 71, 745-746.
12. Kawakami, Y.; Inoue, A.; Kawai, T.; Wakita, M.; Sugimoto, H.; Hopfinger, A.J. The rational for E2020 as a potent acetylcholinesterase inhibitor. Bioorg. Med. Chem. 1996, 4, 1429-1431.
13. Zhou, X.; Wang, X.B.; Wang, T.; Kong, L.Y. Design, synthesis and acetylcholinesterase inhibitory activity of novel coumarin analogues. Bioorg. Med. Chem. 2008, 16, 8011-8021.
14. Ellman, G.L.; Courtney, K.D.; Andres, V.; Featherstone, R.M. A new and rapid colorimetric determination of acetylcholinesterase activity. Biochem. Pharmacol. 1961, 7, 88-95.
15. Kryger, G.; Silman, I.; Sussman, J.L. Structure of acetylcholinesterase complexed with E2020 (Aricept®): Implications for the design of new anti-Alzheimer drugs. Structure 1999, 7, 297-307.