Multitarget Strategy to Address Alzheimer's Disease: Design, Synthesis, Biological Evaluation, and Computational Studies of Coumarin-Based Derivatives

ChemMedChem

Volumn , Issue , 2016, Pages 1296-1308

  Montanari, Serena ^a   Bartolini, Manuela ^a   Neviani, Paolo ^a   Belluti, Federica ^a   Gobbi, Silvia ^a   Pruccoli, Letizia ^a   Tarozzi, Andrea ^a   Falchi, Federico ^b   Andrisano, Vincenza ^a   Miszta, Przemysław ^c   Cavalli, Andrea ^a,b   Filipek, Sławomir ^c   Bisi, Alessandra ^a   Rampa, Angela ^a  

^a UNIVERSITY OF BOLOGNA   (Italy)

^b ISTITUTO ITALIANO DI TECNOLOGIA   (Italy)

^c UNIVERSITY OF WARSAW   (Poland)

Author keywords

Alzheimer's disease; coumarins; cytotoxicity; inhibitors; multitarget directed ligands

Indexed keywords

10 CHLORO 1 METHOXY 11H INDENO[1,2 B ]QUINOLINE; 3 [4 [[BENZYL(ETHYL)AMINO]METHYL]PHENYL] 6 (4 CHLOROBUTOXY) 2H CHROMEN 2 ONE; 3 [4 [[BENZYL(ETHYL)AMINO]METHYL]PHENYL] 6 (4 IODOBUTOXY) 2H CHROMEN 2 ONE; 3 [4 [[BENZYL(ETHYL)AMINO]METHYL]PHENYL] 6 (5 CHLOROPENTYLOXY) 2H CHROMEN 2 ONE; 3 [4 [[BENZYL(ETHYL)AMINO]METHYL]PHENYL] 6 [(5 IODOPENTYL)OXY] 2H CHROMEN 2 ONE; 3 [4 [[BENZYL(ETHYL)AMINO]METHYL]PHENYL] 6 [(5 MORPHOLINOPENTYL)OXY] 2H CHROMEN 2 ONE; 3 [4 [[BENZYL(ETHYL)AMINO]METHYL]PHENYL] 6 [2 [(7 METHOXY 6H INDENO[2,1 B]QUINOLIN 11 YL)MINO]ETHOXY] 2H CHROMEN 2 ONE; 3 [4 [[BENZYL(ETHYL)AMINO]METHYL]PHENYL] 6 [4 (DIETHYLAMINO)BUTOXY] 2H CHROMEN 2 ONE; 3 [4 [[BENZYL(ETHYL)AMINO]METHYL]PHENYL] 6 [[5 (4 PHENYLPIPERAZIN 1 YL)PENTYL]OXY] 2H CHROMEN 2 ONE; 3 [4 [[BENZYL(ETHYL)AMINO]METHYL]PHENYL] 6 [[5 (4 PHENYLPIPERIDIN 1 YL)PENTYL]OXY] 2H CHROMEN 2 ONE; 3 [4 [[BENZYL(ETHYL)AMINO]METHYL]PHENYL] 6 [[5 (DIETHYLAMINO)PENTYL]OXY] 2H CHROMEN 2 ONE; 3 [4 [[BENZYL(ETHYL)AMINO]METHYL]PHENYL] 6 [[5 (PIPERIDIN 1 YL)PENTYL]OXY] 2H CHROMEN 2 ONE; 3 [4 [[BENZYL(ETHYL)AMINO]METHYL]PHENYL] 6 [[5 [(7 METHOXY 6H INDENO[2,1 B]QUINOLIN 11 YL)AMINO]PENTYL]OXY] 2H CHROMEN 2 ONE; 3 [4 [[BENZYL(ETHYL)AMINO]METHYL]PHENYL] 6 [[5 [3,4 DIHYDROISOQUINOLIN 2(1H) YL]PENTYL]OXY] 2H CHROMEN 2 ONE; 3 [4 [[BENZYL(ETHYL)AMINO]METHYL]PHENYL] 7 (4 CHLOROBUTOXY) 2H CHROMEN 2 ONE; 3 [4 [[BENZYL(ETHYL)AMINO]METHYL]PHENYL] 7 (4 IODOBUTOXY) 2H CHROMEN 2 ONE; 3 [4 [[BENZYL(ETHYL)AMINO]METHYL]PHENYL] 7 [(5 CHLOROPENTYL)OXY] 2H CHROMEN 2 ONE; 3 [4 [[BENZYL(ETHYL)AMINO]METHYL]PHENYL] 7 [(5 IODOPENTYL)OXY] 2H CHROMEN 2 ONE; 3 [4 [[BENZYL(ETHYL)AMINO]METHYL]PHENYL] 7 [4 (DIETHYLAMINO)BUTOXY] 2H CHROMEN 2 ONE; 3 [4 [[BENZYL(ETHYL)AMINO]METHYL]PHENYL] 7 [[5 (DIETHYLAMINO)PENTYL]OXY 2H CHROMEN 2 ONE; 6 (5 AMINOPENTYL) 3 [4 [[BENZYL(ETHYL)AMINO]METHYL]PHENYL] 2H CHROMEN 2 ONE; AMYLOID BETA PROTEIN; CHOLINESTERASE INHIBITOR; COUMARIN DERIVATIVE; DONEPEZIL; NEUROPROTECTIVE AGENT; UNCLASSIFIED DRUG;

ALZHEIMER DISEASE; ARTICLE; CELL VIABILITY; CONTROLLED STUDY; DRUG DESIGN; DRUG EFFICACY; DRUG MECHANISM; DRUG SCREENING; DRUG SYNTHESIS; HUMAN; HUMAN CELL; HYDROGEN BOND; IN VITRO STUDY; MOLECULAR DYNAMICS; NEUROPROTECTION; PHYSICAL CHEMISTRY; PRIORITY JOURNAL; STRUCTURE ACTIVITY RELATION;

EID: 84976481264     PISSN: 18607179     EISSN: 18607187     Source Type: Journal    
DOI: 10.1002/cmdc.201500392     Document Type: Article

References (38)

1. C. Ballard, S. Gauthier, A. Corbett, C. Brayne, D. Aarsland, E. Jones, Lancet 2011, 377, 1019–1031.
2. A. Contestabile, Behav. Brain Res. 2011, 221, 334–340.
3. L. A. Craig, N. S. Hong, R. J. McDonald, Neurosci. Biobehav. Rev. 2011, 35, 1397–1409.
4. B. Reisberg, R. Doody, A. Stöffler, F. Schmitt, S. Ferris, H. J. Möbius, N. Engl. J. Med. 2003, 348, 1333–1341.
5. C. L. Masters, D. J. Selkoe, Cold Spring Harbor Perspect. Med. 2012, 2, a006262.
6. J. Avila, FEBS Lett. 2006, 580, 2922–2927.
7. D. J. Selkoe, Behav. Brain Res. 2008, 192, 106–113.
8. J. Hardy, D. J. Selkoe, Science 2002, 297, 353–356.
9. S. T. Ferreira, M. V. Lourenco, M. M. Oliveira, F. G. De Felice, Front. Cell. Neurosci. 2015, 9, 191.
10. H. Fukumoto, T. Tokuda, T. Kasai, N. Ishigami, H. Hidaka, M. Kondo, D. Allsop, M. Nakagawa, FASEB J. 2010, 24, 2716–2726.
11. Y. Gong, L. Chang, K. L. Viola, P. N. Lacor, M. P. Lambert, C. E. Finch, G. A. Krafft, W. L. Klein, Proc. Natl. Acad. Sci. USA 2003, 100, 10417–10422.
12. R. Morphy, Z. Rankovic, Curr. Pharm. Des. 2009, 15, 587–600.
13. A. Rampa, F. Belluti, S. Gobbi, A. Bisi, Curr. Top. Med. Chem. 2011, 11, 2716–2730.
14. R. León, A. G. Garcia, J. Marco-Contelles, Med. Res. Rev. 2013, 33, 139–189.
15. L. Piazzi, A. Rampa, A. Bisi, S. Gobbi, F. Belluti, A. Cavalli, M. Bartolini, V. Andrisano, P. Valenti, M. Recanatini, J. Med. Chem. 2003, 46, 2279–2282.
16. L. Piazzi, A. Cavalli, F. Belluti, A. Bisi, S. Gobbi, S. Rizzo, M. Bartolini, V. Andrisano, M. Recanatini, A. Rampa, J. Med. Chem. 2007, 50, 4250–4254.
17. L. Piazzi, A. Cavalli, F. Colizzi, F. Belluti, M. Bartolini, F. Mancini, M. Recanatini, V. Andrisano, A. Rampa, Bioorg. Med. Chem. Lett. 2008, 18, 423–426.
18. G. L. Ellman, K. D. Courtney, V. Andres, R. M. Featherstone, Biochem. Pharmacol. 1961, 7, 88–95.
19. J. Cheung, M. J. Rudolph, F. Burshteyn„ M. S. Cassidy, E. N. Gary, J. Love, M. C. Franklin, J. J. Height, J. Med. Chem. 2012, 55, 10282–10286.
20. Schrödinger LLC, New York, NYSmall-Molecule Drug Discovery Suite 2014-3: Glide version 6.4, (USA), 2014; www.schrodinger.com/.
21. A. Rampa, A. Bisi, F. Belluti, S. Gobbi, P. Valenti, V. Andrisano, V. Cavrini, A. Cavalli, M. Recanatini, Bioorg. Med. Chem. 2000, 8, 497–506.
22. M. Recanatini, A. Cavalli, F. Belluti, L. Piazzi, A. Rampa, A. Bisi, S. Gobbi, P. Valenti, V. Andrisano, M. Bartolini, V. Cavrini, J. Med. Chem. 2000, 43, 2007–2018.
23. Y. Nicolet, O. Lockridge, P. Masson, J. C. Fontecilla-Camps, F. Nachon, J. Biol. Chem. 2003, 278, 41141–41147.
24. H. Naiki, K. Higuchi, K. Nakakuki, T. Takeda, Lab. Invest. 1991, 65, 104–110.
25. A. Rauk, Dalton Trans. 2008, 1273–1282.
26. Y. Porat, A. Abramowitz, E. Gazit, Chem. Biol. Drug Des. 2006, 67, 27–37.
27. E. Gazit, FASEB J. 2002, 16, 77–83.
28. H. Pajouhesh, R. G. Lenz, NeuroRx 2005, 2, 541–553.
29. M. C. Wenlock, R. P. Austin, P. Burton, A. M. Davis, P. D. Leeson, J. Med. Chem. 2003, 46, 1250–1256.
30. M. Bartolini, C. Bertucci, M. L. Bolognesi, A. Cavalli, C. Melchiorre, V. Andrisano, ChemBioChem 2007, 8, 2152–2161.
31. A. Tarozzi, M. Bartolini, L. Piazzi, L. Valgimigli, R. Amorati, C. Bolondi, A. Djemil, F. Mancini, V. Andrisano, A. Rampa, Pharmacol. Res. Perspect. 2014, 2, e00023.
32. K. Vanommeslaeghe, E. P. Raman, A. D. MacKerell, Jr., J. Chem. Inf. Model. 2012, 52, 3155–3168.
33. T. Luhrs, C. Ritter, M. Adrian, D. Riek-Loher, B. Bohrmann, H. Doeli, D. Schubert, R. Riek, Proc. Natl. Acad. Sci. USA 2005, 102, 17342–17347.
34. S. A. Poulsen, A. A. Watson, D. P. Fairlie, D. J. Craik, J. Struct. Biol. 2000, 130, 142–152.
35. J. C. Phillips, R. Braun, W. Wang, J. Gumbart, E. Tajkhorshid, E. Villa, C. Chipot, R. D. Skeel, L. Kale, K. Schulten, J. Comput. Chem. 2005, 26, 1781–1802.
36. W. Humphrey, A. Dalke, K. Schulten, J. Mol. Graph. Model. 1996, 14, 33–38.
37. R. Kubo, M. Toda, N. Hashitsume, Statistical Physics II: Nonequilibrium Statistical Mechanics, Springer, Berlin, 1991.
38. J. Ryckaert, G. Ciccotti, H. Berendsen, J. Comput. Phys. 1977, 23, 327–341.