Design, synthesis and biological evaluation of coumarin alkylamines as potent and selective dual binding site inhibitors of acetylcholinesterase

Bioorganic and Medicinal Chemistry

Volumn 21, Issue 1, 2013, Pages 146-152

  Catto, Marco ^a   Pisani, Leonardo ^a   Leonetti, Francesco ^a   Nicolotti, Orazio ^a   Pesce, Paolo ^a   Stefanachi, Angela ^a   Cellamare, Saverio ^a   Carotti, Angelo ^a  

^a UNIVERSITY OF BARI   (Italy)

Author keywords

Acetylcholinesterase; Alzheimer's disease; Coumarin derivatives; Dual binding site inhibitors; Selective cholinesterase inhibition

Indexed keywords

3 (1 BENZYLPIPERIDIN 4 YLOXY) 2 OXO 2H CHROMENE; 3 (1 BENZYLPIPERIDIN 4 YLOXY) 6 METHOXY 2 OXO 2H CHROMENE; 3 (1 BENZYLPIPERIDIN 4 YLOXY) 6,7 DIMETHOXY 2 OXO 2H CHROMENE; 3 (1 BENZYLPIPERIDIN 4 YLOXY) 7 METHOXY 2 OXO 2H CHROMENE; 6,7 DIMETHOXY 2 OXO 2H CHROMENE 3 CARBOXYLIC ACID (1 BENZYLPIPERIDIN 4 YL)ESTER; 6,7 DIMETHOXY 2 OXO 2H CHROMENE 3 CARBOXYLIC ACID (4 BENZYLPIPERAZIN 1 YL)AMIDE; 6,7 DIMETHOXY 2 OXO 2H CHROMENE 3 CARBOXYLIC ACID [2 (N BENZYL N METHYLAMINO)ETHYL]AMIDE; 6,7 DIMETHOXY 2 OXO 2H CHROMENE 3 CARBOXYLIC ACID [3 (N BENZYL N METHYLAMINO)PROPYL]AMIDE; 6,7 DIMETHOXY 2 OXO 2H CHROMENE 3 CARBOXYLIC ACID [4 (N BENZYL N METHYLAMINO)BUTYL]AMIDE; 6,7 DIMETHOXY 2 OXO 2H CHROMENE 3 CARBOXYLIC ACID N (1 BENZYLPIPERIDIN 1 YL)AMIDE; ACETYLCHOLINESTERASE; ALIPHATIC AMINE; CHOLINESTERASE INHIBITOR; COUMARIN; COUMARIN ALKYLAMINE DERIVATIVE; DONEPEZIL; UNCLASSIFIED DRUG;

ARTICLE; BIOLOGICAL ACTIVITY; DRUG BINDING SITE; DRUG DESIGN; DRUG MECHANISM; DRUG POTENCY; DRUG SELECTIVITY; DRUG SYNTHESIS; ENZYME ACTIVE SITE; ENZYME INHIBITION; IC 50; STRUCTURE ACTIVITY RELATION;

ACETYLCHOLINESTERASE; ALZHEIMER DISEASE; ANIMALS; BINDING SITES; BUTYRYLCHOLINESTERASE; CATTLE; CHOLINESTERASE INHIBITORS; COUMARINS; HORSES; HUMANS;

EID: 84870943115     PISSN: 09680896     EISSN: 14643391     Source Type: Journal    
DOI: 10.1016/j.bmc.2012.10.045     Document Type: Article

References (31)

1. H.W. Querfurth, and F.M.N. LaFerla N. Eng. J. Med. 362 2010 329
2. A. Corbett, J. Smith, and C. Ballard Expert Rev. Neurother. 12 2012 535
3. A. Martorana, Z. Esposito, and G. Koch CNS Neurosci. Ther. 16 2010 235
4. H.O. Tayeb, H.D. Yang, B.H. Price, and F.I. Tarazi Pharmacol. Ther. 134 2012 8
5. I.E. Orhan, G. Orhan, and E. Gurkas Mini-Rev. Med. Chem. 11 2011 836
6. D.R. Bevan, F. Donati, and A.F. Kopman Anesthesiology 77 1992 785
7. M.N. Meriggioli, and D.B. Sanders Lancet 8 2009 475
8. S.J. McKinnon, L.D. Goldberg, P. Peeples, J.G. Walt, and T.J. Bramley Am. J. Manag. Care 14 2008 S20
9. http://www.rcsb.org/pdb/home/home.do.
10. F. Leonetti, M. Catto, O. Nicolotti, L. Pisani, A. Cappa, A. Stefanachi, and A. Carotti Bioorg. Med. Chem. 16 2008 7450
11. P.R. Carlier, Y.F. Han, E.S.H. Chow, C.P.L. Li, H. Wang, T.X. Lieu, H.S. Wong, and Y.P. Pang Bioorg. Med. Chem. 7 1999 351
12. P. Camps, and D. Muñoz-Torrero Mini-Rev. Med. Chem. 1 2001 163
13. S. Gemma, E. Gabellieri, P. Huleatt, C. Fattorusso, M. Borriello, B. Catalanotti, S. Butini, M. De Angelis, E. Novellino, V. Nacci, T. Belinskaya, A. Saxena, and G. Campiani J. Med. Chem. 49 2006 3421
14. M.L. Bolognesi, R. Matera, A. Minarini, M. Rosini, and C. Melchiorre Curr. Opin. Chem. Biol. 13 2009 303
15. M.L. Bolognesi, M. Rosini, V. Andrisano, M. Bartolini, A. Minarini, V. Tumiatti, and C. Melchiorre Curr. Pharm. Des. 15 2009 601
16. L. Pisani, M. Catto, F. Leonetti, O. Nicolotti, A. Stefanachi, F. Campagna, and A. Carotti Curr. Med. Chem. 18 2011 4568
17. L. Costantino, and D. Barlocco Curr. Med. Chem. 19 2012 3353
18. L. Pisani, M. Catto, I. Giangreco, F. Leonetti, O. Nicolotti, A. Stefanachi, S. Cellamare, and A. Carotti Chem. Med. Chem. 5 2010 1616
19. C. Gnerre, M. Catto, F. Leonetti, P. Weber, P.A. Carrupt, C. Altomare, A. Carotti, and B. Testa J. Med. Chem. 43 2000 4747
20. M. Catto, O. Nicolotti, F. Leonetti, A. Carotti, A.D. Favia, R. Soto-Otero, E. Méndez-Álvarez, and A. Carotti J. Med. Chem. 49 2006 4912
21. L. Pisani, G. Muncipinto, T.F. Miscioscia, O. Nicolotti, F. Leonetti, M. Catto, C. Caccia, P. Salvati, R. Soto-Otero, E. Mendez-Alvarez, C. Passeleu, and A. Carotti J. Med. Chem. 52 2009 6685
22. C. Brühlmann, F. Ooms, P.A. Carrupt, B. Testa, M. Catto, F. Leonetti, C. Altomare, and A. Carotti J. Med. Chem. 44 2001 3195
23. P. Anand, B. Singh, and N. Nirmal Singh Bioorg. Med. Chem. 20 2012 1175
24. G.L. Ellman, K.D. Courtney, V. Andres Jr., and R.M.A. Featherstone Biochem. Pharmacol. 7 1961 88
25. F.M. Dean, A. Robertson, and W.B. Whalley J. Chem. Soc. 1950 895
26. G. Kokotos, and C. Tzougraki J. Heterocycl. Chem. 23 1986 87
27. Y.A. Jackson Heterocycles 1995 1979 9
28. K.N.F. Shaw, A. McMillan, and M.D. Armstrong J. Org. Chem. 21 1956 601
29. H.A. Offe, and H. Jatzkewitz Chem. Ber. 80 1947 469
30. H. Sugimoto, Y. Iimura, Y. Yamanishi, and K. Yamatsu J. Med. Chem. 38 1995 4821
31. N.C. Inestrosa, A. Alvarez, C.A. Perez, R.D. Moreno, M. Vicente, C. Linker, O.I. Casanueva, C. Soto, and J. Garrido Neuron 16 1996 881