Synthesis, biological assessment, and molecular modeling of racemic 7-aryl-9,10,11,12-tetrahydro-7H-benzo[7,8]chromeno[2,3-b]quinolin-8-amines as potential drugs for the treatment of Alzheimer's disease

European Journal of Medicinal Chemistry

Volumn 54, Issue , 2012, Pages 750-763

  Maalej, Emna ^a   Chabchoub, Fakher ^a   Oset Gasque, María Jesús ^b,c   Esquivias Pérez, Mario ^b   González, María P ^b   Monjas, Leticia ^d   Pérez, Concepción ^d   De Los Ríos, Cristóbal ^e   Rodríguez Franco, María Isabel ^d   Iriepa, Isabel ^f   Moraleda, Ignacio ^f   Chioua, Mourad ^g   Romero, Alejandro ^c   Marco Contelles, José ^g   Samadi, Abdelouahid ^g  

^a UNIVERSITY OF SFAX   (Tunisia)

^b UNIVERSIDAD COMPLUTENSE DE MADRID   (Spain)

^c UNIVERSIDAD COMPLUTENSE DE MADRID   (Spain)

^d INSTITUTO DE QUÍMICA MÉDICA   (Spain)

^e HOSPITAL UNIVERSITARIO DE LA PRINCESA   (Spain)

^f UNIVERSITY OF ALCALÁ   (Spain)

^g INSTITUTO DE QUÍMICA ORGÁNICA GENERAL   (Spain)

Author keywords

7 Aryl 9,10,11,12 tetrahydro 7H benzo 7,8 chromeno 2,3 b quinolin 8 amines; Alzheimer's disease; Antioxidant; hAChE; hBuChE; Inhibition mechanism; Kinetic analysis; Molecular modeling; Neuroprotection; ORAC; Toxicity

Indexed keywords

2 AMINO 4 (2 METHOXYPHENYL) 4H BENZO[H]CHROMENE 3 CARBONITRILE; 2 AMINO 4 (2,4 DIMETHOXYPHENYL) 4H BENZO[H]CHROMENE 3 CARBONITRILE; 2 AMINO 4 (2,6 DICHLOROPHENYL) 4H BENZO[H]CHROMENE 3 CARBONITRILE; 2 AMINO 4 (3,4 DICHLOROPHENYL) 4H BENZO[H]CHROMENE 3 CARBONITRILE; 2 AMINO 4 ARYL 4H BENZO[H]CHROMENE 3 CARBONITRILE; 4 (8 AMINO 9,10,11,12 TETRAHYDRO 7H BENZO[7,8]CHROMENO[2,3 B]QUINOLIN 7 YL) 2 METHOXYPHENOL; 4 (8 AMINO 9,10,11,12 TETRAHYDRO 7H BENZO[7,8]CHROMENO[2,3 B]QUINOLIN 7 YL)PHENOL; 7 (2 METHOXYPHENYL) 9,10,11,12 TETRAHYDRO 7H BENZO[7,8]CHROMENO[2,3 B]QUINOLIN 8 AMINE; 7 (2,4 DIMETHOXYPHENYL) 9,10,11,12 TETRAHYDRO 7H BENZO[7,8]CHROMENO[2,3 B]QUINOLIN 8 AMINE; 7 (2,6 DICHLOROPHENYL) 9,10,11,12 TETRAHYDRO 7H BENZO[7,8]CHROMENO[2,3 B]QUINOLIN 8 AMINE; 7 (3,4 DICHLOROPHENYL) 9,10,11,12 TETRAHYDRO 7H BENZO[7,8]CHROMENO[2,3 B]QUINOLIN 8 AMINE; 7 (3,4,5 TRIMETHOXYPHENYL) 9,10,11,12 TETRAHYDRO 7H BENZO[7,8]CHROMENO[2,3 B]QUINOLIN 8 AMINE; 7 (4 NITROPHENYL) 9,10,11,12 TETRAHYDRO 7H BENZO[7,8]CHROMENO[2,3 B]QUINOLIN 8 AMINE; 7 (PARA TOLYL) 9,10,11,12 TETRAHYDRO 7H BENZO[7,8]CHROMENO[2,3 B]QUINOLIN 8 AMINE; 7 ARYL 9,10,11,12 TETRAHYDRO 7H BENZO[7,8]CHROMENO[2,3 B]QUINOLIN 8 AMINE DERIVATIVE; 7 PHENYL 9,10,11,12 TETRAHYDRO 7H BENZO[7,8]CHROMENO[2,3 B]QUINOLIN 8 AMINE; CYCLOHEXANONE; NEUROPROTECTIVE AGENT; TACRINE; UNCLASSIFIED DRUG;

ALZHEIMER DISEASE; ARTICLE; BLOOD BRAIN BARRIER; BRAIN CELL; CELL LINE; CELL VIABILITY; CONTROLLED STUDY; DRUG MECHANISM; DRUG STRUCTURE; DRUG SYNTHESIS; HUMAN; HUMAN CELL; NERVE CELL CULTURE; NEUROPROTECTION; NEUROTOXICITY;

ACETYLCHOLINESTERASE; ALZHEIMER DISEASE; ANIMALS; ANTIOXIDANTS; BLOOD-BRAIN BARRIER; BUTYRYLCHOLINESTERASE; CHEMISTRY TECHNIQUES, SYNTHETIC; CHOLINESTERASE INHIBITORS; ELECTRON TRANSPORT COMPLEX I; ELECTRON TRANSPORT COMPLEX IV; HEP G2 CELLS; HUMANS; KINETICS; MODELS, MOLECULAR; NEUROPROTECTIVE AGENTS; PERMEABILITY; QUINOLINES; RATS; REACTIVE OXYGEN SPECIES; STEREOISOMERISM;

EID: 84864405123     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2012.06.038     Document Type: Article

References (66)

1. M. Goedert, and M.G.A. Spillantini Science 314 2006 777 781
2. A. Castro, and A. Martínez Curr. Pharm. Des. 12 2006 4377 4387
3. J.L. Cummings Rev. Neurol. Dis. 1 2004 60 69
4. E. Scarpini, P. Scheltens, and H. Feldman Lancet Neurol. 2 2003 539 547
5. V.N. Talesa Mech. Ageing Dev. 122 2001 1961 1969
6. M. Racchi, M. Mazzucchelli, E. Porrello, C. Lanni, and S. Govoni Pharmacol. Res. 50 2004 441 451
7. N.C. Inestrosa, A. Álvarez, C.A. Pérez, R.D. Moreno, M. Vicente, C. Linker, O.I. Casanueva, C. Soto, and J. Garrido Neuron 16 1996 881 891
8. M. Bartolini, C. Bertucci, V. Cavrini, and V. Andrisano Biochem. Pharmacol. 65 2003 407 416
9. L. Piazzi, A. Cavalli, F. Colizzi, F. Belluti, M. Bartolini, F. Mancini, M. Recanatini, V. Andrisano, and A. Rampa Bioorg. Med. Chem. Lett. 18 2008 423 426
10. D. Muñoz-Torrero, and P. Camps Curr. Med. Chem. 13 2006 399 422
11. L. Savini, A. Gaeta, C. Fattorusso, B. Catalanotti, G. Campiani, L. Chiasserini, C. Pellerano, E. Novellino, D. McKissic, and A. Saxena J. Med. Chem. 46 2003 1 4
12. P.R. Carlier, E.S. Chow, Y. Han, J. Liu, J. El Yazal, and Y.P. Pang J. Med. Chem. 42 1999 4225 4231
13. R. León, A.G. García, J. Marco-Contelles, Med. Res. Rev. in press.
14. A. Cavalli, M.L. Bolognesi, A. Minarini, M. Rosini, V. Tumiatti, M. Recanatini, and C. Melchiorre J. Med. Chem. 51 2008 347 372
15. L. Fang, D. Appenroth, M. Decker, M. Kiehntopf, C. Roegler, T. Deufel, C. Fleck, S. Peng, Y. Zhang, and J. Lehmann J. Med. Chem. 51 2008 713 716
16. A. Samadi, M. Chioua, I. Bolea, C. de los Ríos, I. Iriepa, I. Moraleda, A. Bastida, G. Esteban, M. Unzeta, E. Gálvez, and J. Marco-Contelles Eur. J. Med. Chem. 46 2011 4665 4668
17. I. Bolea, J. Juárez-Jiménez, C. de los Ríos, M. Chioua, R. Pouplana, F.J. Luque, M. Unzeta, J. Marco-Contelles, and A. Samadi J. Med. Chem. 54 2011 8251 8270
18. N. Toda, K. Tago, S. Marumoto, K. Takami, M. Ori, N. Yamada, K. Koyama, S. Naruto, K. Abe, R. Yamazaki, T. Hara, A. Aoyagi, Y. Abe, T. Kaneko, and H. Kogen Bioorg. Med. Chem. 11 2003 4389 4415
19. M. Rosini, A. Antonello, A. Cavalli, M.L. Bolognesi, A. Minarini, G. Marucci, E. Poggesi, A. Leonardi, and C. Melchiorre J. Med. Chem. 46 2003 4895 4903
20. P.W. Elsinghorst, J.S. Cieslik, K. Mohr, C. Tränkle, and M. Gütschow J. Med. Chem. 50 2007 5685 5695
21. C. de los Ríos, J. Egea, J. Marco-Contelles, R. León, A. Samadi, I. Iriepa, I. Moraleda, E. Gálvez, A.G. García, M.G. López, M. Villarroya, and A. Romero J. Med. Chem. 53 2010 5129 5143
22. M.P. Mattson, B. Cheng, D. Davis, K. Bryant, I. Lieberburg, and R.E. Rydel J. Neurosci. 12 1992 376 389
23. M.F. Cano-Abad, M. Villarroya, A.G. García, N.H. Gabilán, and M.G. López J. Biol. Chem. 276 2001 39695 39704
24. M. Sobrado, M.G. López, F. Carceller, A.G. García, and J.M. Roda Neuroscience 118 2003 107 113
25. R. León, and J. Marco-Contelles Curr. Med. Chem. 11 2011 552 576
26. M. Bartolini, M. Pistolozzi, V. Andrisano, J. Egea, M.G. López, I. Iriepa, I. Moraleda, E. Gálvez, J. Marco-Contelles, and A. Samadi ChemMedChem 6 2011 1990 1997
27. E. Maalej, F. Chabchoub, A. Samadi, C. de los Ríos, A. Perona, A. Morreale, and J. Marco- Contelles Bioorg. Med. Chem. Lett. 21 2011 2384 2388
28. J. Li, L. Zhang, D. Shi, Q. Li, D. Wang, C. Wang, Q. Zhang, L. Zhang, and Y. Fan Synlett 2008 233 236
29. N. Panner-Selvam, T.H. Babu, and P.T. Perumal Tetrahedron 65 2009 8524 8530
30. 2-Amino-4-phenyl-4H-benzo[h]chromene-3-carbonitrile (11), 2-amino-4-(4-hydroxyphenyl)-4H-benzo[h]chromene-3-carbonitrile (13), 2-amino-4-(4-hydroxy-3-methoxyphenyl)-4H-benzo[h]chromene-3-carbonitrile (15), and 2-amino-4-(3,4,5-trimethoxyphenyl)-4H-benzo[h]chromene-3-carbonitrile (17) have been described in: A. Patra, and T. Mahapatra J. Chem. Res. (S) 2008 405 408
31. 2-Amino-4-(p-tolyl)-4H-benzo[h]chromene-3-carbonitrile (12), 2-amino-4-(4-nitrophenyl)-4H-benzo[h]chromene-3-carbonitrile (18) have been reported in: J.M. Khurana, B. Nand, and P. Saluja Tetrahedron 66 2010 5637 5641
32. 2-Amino-4-(2-methoxyphenyl)-4H-benzo[h]chromene-3-carbonitrile (14): X. Wang, X. Xu, Z. Quan, and Z. Zhang Youji Huaxue 29 2009 1821 1824
33. 2-Amino-4-(3,4-dichlorophenyl)-4H-benzo[h]chromene-3-carbonitrile (20): A.C. Williams, (1994) EP 618206.
34. X.-S. Wang, Z.-S. Zeng, Y.-L. Li, D.-Q. Shi, S.-J. Tu, X.-Y. Wei, and Z.-M. Zong Synth. Commun. 35 2005 1915 1920
35. M.S. Al-Said, M.M. Ghorab, S.I. Al-Qasoumi, E.M. El-Hossary, and E. Noaman Eur. J. Med. Chem. 45 2010 3011 3018
36. J.L. Soto, C. Seoane, P. Zamorano, and F.J. Cuadrado Synthesis 1981 529 530
37. L. Jedinak, V. Krystof, and P. Cankar Heterocycles 83 2011 371 383
38. J. Marco-Contelles, M.E. Pérez-Mayoral, A. Samadi, M.C. Carreiras, and E. Soriano Chem. Rev. 109 2009 2652 2671
39. G.L. Ellman, K.D. Courtney, B.J. Andres, and R.M. Featherstone Biochem. Pharmacol. 7 1961 88 95
40. L. Di, E.H. Kerns, K. Fan, O.J. McConnell, and G.T. Carter Eur. J. Med. Chem. 38 2003 223 232
41. M.I. Fernández-Bachiller, C. Pérez, N.E. Campillo, J.A. Páez, G.C. González-Muñoz, P. Usán, E. García-Palomero, M.G. López, M. Villarroya, A.G. García, A. Martínez, and M.I. Rodríguez-Franco ChemMedChem 4 2009 828 841
42. G.C. González-Muñoz, M.P. Arce, B. López, C. Pérez, A. Romero, L. del Barrio, M.D. Martín-de-Saavedra, J. Egea, R. León, M. Villarroya, M.G. López, A.G. García, S. Conde, and M.I. Rodríguez-Franco Eur. J. Med. Chem. 46 2011 2224 2235
43. M.I. Fernández-Bachiller, C. Pérez, G.C. González-Muñoz, S. Conde, M.G. López, M. Villarroya, A.G. García, and M.I. Rodríguez-Franco J. Med. Chem. 53 2010 4927 4937
44. E. Viayna, T. Gómez, C. Galdeano, L. Ramírez, M. Ratia, A. Badia, M.V. Clos, E. Verdaguer, F. Junyent, A. Camins, M. Pallàs, M. Bartolini, F. Mancini, V. Andrisano, M.P. Arce, M.I. Rodríguez-Franco, A. Bidon-Chanal, F.J. Luque, P. Camps, and D. Muñoz-Torrero ChemMedChem 5 2010 1855 1870
45. G.C. González-Muñoz, M.P. Arce, C. Pérez, M. Villarroya, M.G. López, A.G. García, S. Conde, and M.I. Rodríguez-Franco Eur. J. Med. Chem. 45 2010 6152 6158
46. P. Camps, X. Formosa, C. Galdeano, D. Muñoz-Torrero, L. Ramírez, E. Gómez, N. Isambert, R. Lavilla, A. Badia, M.V. Clos, M. Bartolini, F. Mancini, V. Andrisano, M.P. Arce, M.I. Rodríguez-Franco, O. Huertas, T. Dafni, and F.J. Luque J. Med. Chem. 52 2009 5365 5379
47. J. Marco-Contelles, R. León, C. de los Ríos, A. Samadi, M. Bartolini, V. Andrisano, O. Huertas, X. Barril, F.J. Luque, M.I. Rodríguez-Franco, B. López, M.G. López, A.G. García, M. Carreiras, and M. Villarroya J. Med. Chem. 52 2009 2724 2732
48. F. Reviriego, M.I. Rodríguez-Franco, P. Navarro, E. García-España, M. Liu-González, B. Verdejo, and A. Domènech J. Am. Chem. Soc. 128 2006 16458 16459
49. F.J. Pavón, L. Hernández-Folgado, A. Bilbao, A. Cippitelli, N. Jagerovic, G. Abellán, M.I. Rodríguez-Franco, A. Serrano, M. Macías, M. Navarro, P. Goya, and F. Rodríguez de Fonseca Neuropharmacology 51 2006 358 366
50. M.I. Fernández-Bachiller, C. Pérez, L. Monjas, J. Rademann, and M.I. Rodríguez-Franco J. Med. Chem. 55 2012 1303 1317
51. B. Ou, M. Hampsch-Woodill, and R.L. Prior J. Agric. Food Chem. 49 2001 4619 4626
52. A. Dávalos, C. Gómez-Cordobés, and B. Bartolomé J. Agric. Food Chem. 52 2004 48 54
53. M.I. Rodríguez-Franco, M.I. Fernández-Bachiller, C. Pérez, B. Hernández-Ledesma, and B. Bartolomé J. Med. Chem. 49 2006 459 462
54. E. Sofic, Z. Rimpapa, Z. Kundurovic, A. Sapcanin, I. Tahirovic, A. Rustembegoric, and G. Cao J. Neural Transm. 112 2005 349 358
55. W.G. Blackard Jr., G.K. Sood, D.R. Crowe, and M.B. Fallon J. Clin. Gastroenterol. 26 1998 57 59
56. F. Denizot, and R. Lang J. Immunol. Methods 89 1986 271 277
57. S.I. Gracon, M.J. Knapp, W.G. Berghoff, M. Pierce, R. de Jong, S.J. Lobbestael, J. Symons, S.L. Dombey, F.A. Luscombe, and D. Kraemer Alzheimer Dis. Assoc. Disord. 12 1998 93 101
58. N. Cañas, T. Valero, M. Villarroya, E. Montell, J. Vergés, A.G. García, and M.G. López J. Pharmacol. Exp. Ther. 323 2007 946 953
59. M. Chioua, D. Sucunza, E. Soriano, D. Hadjipavlou-Litina, A. Alcázar, I. Ayuso, M.J. Oset-Gasque, M.P. González, L. Monjas, M.I. Rodríguez-Franco, J. Marco-Contelles, and A. Samadi J. Med. Chem. 55 2012 153 168
60. A. Samadi, E. Soriano, J. Revuelta, C. Valderas, M. Chioua, I. Garrido, B. Bartolomé, I. Tomassolli, L. Ismaili, L. González-Lafuente, M. Villarroya, A.G. García, M.J. Oset-Gasque, and J. Marco-Contelles Bioorg. Med. Chem. 19 2011 951 960
61. C. Arce, J.L. Arteaga, E. Sánchez-Mendoza, M.J. Oset-Gasque, S. Cañadas, and M.P. González Neurosci. Med. 1 2010 50 59
62. S. Figueroa, S. Cañadas, C. Arce, M.J. Oset-Gasque, and M.P. González Brain Res. 1047 2005 168 176
63. O. Trott, and A.J. Olson J. Comput. Chem. 31 2010 455 461
64. C. Martins, M.C. Carreiras, R. Leon, C. de los Ríos, M. Bartolini, V. Andrisano, I. Iriepa, I. Moraleda, E. Gálvez, M.G. García, J. Egea, A. Samadi, M. Chioua, and J. Marco-Contelles Eur. J. Med. Chem. 46 2011 6119 6130
65. B.R. Brooks, R.E. Bruccoleri, B.D. Olafson, D.J. States, S. Swaminathan, and M. Karplus J. Comput. Chem. 4 1983 187 217
66. A. Morreale, F. Maseras, I. Iriepa, and E. Gálvez J. Mol. Graphics Modell. 21 2002 111 118