Synthesis of novel cognition enhancers with pyrazolo[5,1-c][1,2,4] benzotriazine core acting at γ-aminobutyric acid type A (GABAA) receptor

Bioorganic and Medicinal Chemistry

Volumn 21, Issue 8, 2013, Pages 2186-2198

  Guerrini, Gabriella ^a   Ciciani, Giovanna ^a   Costanzo, Annarella ^a   Daniele, Simona ^b   Martini, Claudia ^b   Ghelardini, Carla ^a   Di Cesare Mannelli, Lorenzo ^a   Ciattini, Samuele ^a  

^a UNIVERSITY OF FLORENCE   (Italy)

^b UNIVERSITY OF PISA   (Italy)

Author keywords

Binding affinity; Cognition enhancing activity; GABAA receptors; Pyrazolo 5,1 c 1,2,4 benzotriazine system

Indexed keywords

3 (1,2,4 OXADIAZOL 3 METHYL 5 YL) 8 (PYRIDIN 4 YLMETHOXY)PYRAZOLO[5,1 C][1,2,4] BENZOTRIAZINE 5 OXIDE; 3 (1,2,4 OXADIAZOL 3 METHYL 5 YL) 8 (THIEN 2 YLMETHOXY)PYRAZOLO[5,1 C][1,2,4]BENZO TRIAZINE 5 OXIDE; 3 (1,2,4 OXADIAZOL 3 METHYL 5 YL) 8 BENZYLOXYPYRAZOLO[5,1 C][1,2,4]BENZOTRIAZINE 5 OXIDE; 3 (1,2,4 TRIAZOL 1 METHYL 3 YL) 8 BENZYLOXYPYRAZOLO[5,1 C][1,2,4]BENZOTRIAZINE 5 OXIDE; 3 (1,2,4 TRIAZOL 1 METHYL 5 YL) 8 BENZYLOXYPYRAZOLO[5,1 C][1,2,4]BENZOTRIAZINE 5 OXIDE; 3 (1,2,4 TRIAZOL 3 YL) 8 (PYRIDIN 4 YLMETHOXY)PYRAZOLO[5,1 C][1,2,4]BENZOTRIAZINE 5 OXIDE; 3 (1,2,4 TRIAZOL 3 YL) 8 BENZYLOXYPYRAZOLO[5,1 C][1,2,4]BENZOTRIAZINE 5 OXIDE; 3 [N (DIMETHYLAMINOMETHYLENE)CARBAMOYL] 8 (PYRIDIN 4 YLMETHOXY)PIRAZOLO[5,1 C][1,2,4]BENZOTRIAZINE 5 OXIDE; 3 [N (DIMETHYLAMINOMETHYLENE)CARBAMOYL] 8 (THIEN 2 YLMETHOXY)PYRAZOLO[5,1 C][1,2,4]BENZOTRIAZINE 5 OXIDE; 3 [N (DIMETHYLAMINOMETHYLENE)CARBAMOYL] 8 BENZYLOXYPYRAZOLO[5,1 C][1,2,4] BENZOTRIAZINE 5 OXIDE; 3 CARBAMOYL 8 (PYRIDIN 4 YLMETHOXY)PYRAZOLO[5,1 C][1,2,4]BENZOTRIAZINE 5 OXIDE; 3 CARBAMOYL 8 (THIEN 2 YLMETHOXY)PYRAZOLO[5,1 C] [1,2,4]BENZOTRIAZINE 5 OXIDE; 3 CARBAMOYL 8 BENZYLOXYPYRAZOLO[5,1 C][1,2,4]BENZOTRIAZINE 5 OXIDE; 3 IODO 8 (1 OXIDOPYRIDIN 4 YLMETHOXY)PYRAZOLO[5,1 C][1,2,4]BENZOTRIAZINE 5 OXIDE; 3 IODO 8 (FUR 2 YLMETHYLAMINO)PYRAZOLO[5,1 C][1,2,4]BENZOTRIAZINE 5 OXIDE; 3 IODO 8 (PYRIDIN 2 YLMETHYLAMINO)PYRAZOLO[5,1 C][1,2,4]BENZOTRIAZINE 5 OXIDE; 3 IODO 8 (PYRIDIN 3 YLMETHYLAMINO)PYRAZOLO[5,1 C][1,2,4]BENZOTRIAZINE 5 OXIDE; 3 IODO 8 (PYRIDIN 4 YLMETHYLAMINO)PYRAZOLO[5,1 C][1,2,4]BENZOTRIAZINE 5 OXIDE; 3 METHYL 8 (PYRIDIN 4 YLMETHYLOXY)PYRAZOLO[5,1 C][1,2,4]BENZOTRIAZINE 5 OXIDE; 3 METHYL 8 CHLOROPYRAZOLO[5,1 C][1,2,4]BENZOTRIAZINE; 3 METHYL 8 CHLOROPYRAZOLO[5,1 C][1,2,4]BENZOTRIAZINE 5 OXIDE; 4 AMINOBUTYRIC ACID A RECEPTOR; DIAZEPAM; PIRACETAM; PYRAZOLO[5,1 C][1,2,4]BENZOTRIAZINE DERIVATIVE; TRIAZINE DERIVATIVE; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ANTIAMNESIC ACTIVITY; ARTICLE; CONTROLLED STUDY; DRUG ACTIVITY; DRUG SYNTHESIS; IN VITRO STUDY; IN VIVO STUDY; LEARNING; MALE; MEMORY; MOUSE; NONHUMAN; PASSIVE AVOIDANCE; PROCOGNITIVE ACTIVITY; PROMNEMONIC ACTIVITY; RAT; TRANQUILIZING ACTIVITY;

ANIMALS; BEHAVIOR, ANIMAL; CATTLE; CRYSTALLOGRAPHY, X-RAY; GAMMA-AMINOBUTYRIC ACID; KINETICS; LEARNING; LIGANDS; MALE; MEMORY; MICE; MODELS, ANIMAL; RATS; RATS, WISTAR; RECEPTORS, GABA-A; STRUCTURE-ACTIVITY RELATIONSHIP; TRIAZINES;

EID: 84875706001     PISSN: 09680896     EISSN: 14643391     Source Type: Journal    
DOI: 10.1016/j.bmc.2013.02.027     Document Type: Article

References (62)

1. R.A. Rissman, and W.C. Mobley J. Neurochem. 117 2011 613
2. R.A. Rissman, A.L. De Blas, and D.M. Armstrong J. Neurochem. 103 2007 1285
3. A. Limon, J.M. Reyes-Ruiz, and R. Miledi Future Med. Chem. 3 2011 149
4. T.L. Wallace, T.M. Ballard, B. Pouzet, W.J. Riedel, and J.G. Wettstein Pharmacol. Biochem. Behav. 99 2011 130
5. C.H. Vinkers, N.R. Mirza, B. Olivier, and R.S. Kahn Expert Opin. Investig. Drugs 19 2010 1217
6. E.I. Charych, F. Liu, S.J. Moss, and N.J. Brandon Neuropharmacology 57 2009 481
7. N. Ibarretxe-Bilbao, M. Zarei, C. Junque, M.J. Marti, B. Segura, P. Vendrell, F. Valldeoriola, N. Bargallo, and E. Tolosa NeuroImage 57 2011 589
8. M.B.H. Youdim, and J.J. Buccafusco J. Neural Transm. 112 2005 519
9. Potier, M.-C.; Dodd, R.; Delatur, B.; Braudeau, J.; Herault, Y. WO2011024115, 2011.
10. J.R. Atack Curr. Top. Med. Chem. 11 2011 1203
11. H. Mohler Biochem. Soc. Trans. 037 2009 1328
12. R.W. Olsen, and W. Sieghart Pharmacol. Rev. 60 2008 243
13. R.W. Olsen, and W. Sieghart Neuropharmacology 56 2009 141
14. G.L. Collingridge, R.W. Olsen, J. Peters, and M. Spedding Neuropharmacology 56 2009 2
15. U. Rudolph, and H. Mohler Annu. Rev. Pharmacol. Toxicol. 44 2004 475
16. U. Rudolph, and H. Mohler Curr. Opin. Pharmacol. 6 2006 1
17. P.J. Whiting Curr. Opin. Pharmacol. 6 2006 24
18. C. D'Hulst, J.R. Atack, and R.F. Kooy Drug Discovery Today 14 2009 866
19. R.M. McKernan, T.W. Rosahl, D.S. Reynolds, C. Sur, K.A. Wafford, J.R. Atack, S. Farrar, J. Myers, G. Cook, P. Ferris, L. Garrett, L. Bristow, G. Marshall, A. Macaulay, N. Brown, O. Howell, K.W. Moore, R.W. Carling, L.J. Street, J.L. Castro, C.I. Ragan, G.R. Dawson, and P.J. Whiting Nat. Neurosci. 3 2000 587
20. B. Ebert, K.A. Wafford, and S. Deacon Pharmacol. Ther. 112 2006 612
21. M.M. Savic, D.I. Obradovic, N.D. Ugresic, and D.R. Bokonjic Neural Plast. 12 2005 289
22. J.R. Atack Curr. Top. Med. Chem. 11 2011 1176
23. D.S. Reynolds Pharmacol. Biochem. Behav. 90 2008 37
24. B.K. Yee, R. Keist, L. von Boehmer, R. Studer, D. Benke, N. Hagenbuch, Y. Dong, R.C. Malenka, J.-M. Fritschy, H. Bluethmann, J. Feldon, H. Mohler, and U. Rudolph PNAS 102 2005 17154
25. V.B. Caraiscos, E.M. Elliott, K.E. You-Ten, V.Y. Cheng, D. Belelli, J.G. Newell, M.F. Jackson, J.J. Lambert, T.W. Rosahl, K.A. Wafford, J.F. MacDonald, and B.A. Orser PNAS 101 2004 3662
26. W. Sieghart Drugs Future 31 2006 685
27. W. Sieghart Adv. Pharmacol. 54 2006 231
28. S. Pappatà, A. Varrone, C. Vicidomini, G. Milan, C. De Falco, V. Sansone, A. Iavarone, M. Comerci, E. Lorè, M. Panico, M. Quarantelli, A. Postiglione, and M. Salvatore Eur. J. Nucl. Med. Mol. Imaging 2010 1156
29. O. Howell, J.R. Atack, D. Dewar, R.M. McKernan, and C. Sur Neuroscience 98 2000 669
30. M.S. Chambers, J.R. Atack, R.W. Carling, N. Collinson, S.M. Cook, G.R. Dawson, P. Ferris, S.C. Hobbs, D. O'Connor, G. Marshall, W. Rycroft, and A.M. MacLeod J. Med. Chem. 47 2004 5829
31. Guerrini, G.; Ciciani, G. Constitutive Activity in Receptors and Other Proteins, Part B; Vol. 485 ed.; Academic Press, San Diego, CA. 92101-4495, 2010; pp 197-211.
32. K. Maubach Drugs Future 31 2006 151
33. K. Quirk, P. Blurton, S. Fletcher, P. Leeson, F. Tang, D. Melillo, C.I. Ragan, and R.M. McKernan Neuropharmacol 35 1996 1331
34. F. Sternfeld, R.W. Carling, R.A. Jelley, T. Ladduwahetty, K.J. Merchant, K.W. Moore, A.J. Reeve, L.J. Street, D. O'Connor, B. Sohal, J.R. Atack, S. Cook, G. Seabrook, K.A. Wafford, D. Tattersall, N. Collinson, G.R. Dawson, J.L. Castro, and A.M. MacLeod J. Med. Chem. 47 2004 2176
35. Chambers, M. S.; Jones, P.; MacLeod, A. M.; Maxey, R.; Szekeres, H. J. WO200242305, 2002.
36. Buettelmann, B.; Dong, J.; Han, B.; Knust, H.; Thomas, A. WO2007074089, 2007.
37. B. Buettelmann, T.M. Ballard, R. Gasser, H. Fischer, M.-C. Hernandez, F. Knoflach, H. Knust, H. Stadler, A.W. Thomas, and G. Trube Bioorg. Med. Chem. Lett. 19 2009 5958
38. L.J. Street, F. Sternfeld, R.A. Jelley, A.J. Reeve, R.W. Carling, K.W. Moore, R.M. McKernan, B. Sohal, S. Cook, A. Pike, G.R. Dawson, F.A. Bromidge, K.A. Wafford, G. Seabrook, S.A. Thompson, G. Marshall, G.V. Pillai, J.L. Castro, J.R. Atack, and A.M. MacLeod J. Med. Chem. 47 2004 3642
39. J.R. Atack, K. Maubach, K.A. Wafford, D. O'Connor, A.D. Rodrigues, D.C. Evans, D. Tattersall, M.S. Chambers, A.M. MacLeod, W. Eng, C. Ryan, E. Hostetler, S.M. Sanabria, R.M. Gibson, S. Krause, H.D. Burns, R.J. Hargreaves, N.G.B. Agrawal, R.M. McKernan, M.G. Murphy, K. Gingrich, G.R. Dawson, D.G. Musson, and K.J. Petty J. Pharmacol. Exp. Ther. 331 2009 470
40. G.R. Dawson, K. Maubach, N. Collinson, M. Cobain, B.J. Everitt, A.M. MacLeod, H.I. Choudhury, L.M. McDonald, G.V. Pillai, W. Rycroft, A.J. Smith, F. Sternfeld, D. Tattersall, K.A. Wafford, D.S. Reynolds, G. Seabrook, and J.R. Atack JPET 316 2006 1335
41. G. Guerrini, G. Ciciani, G. Cambi, F. Bruni, S. Selleri, C. Guarino, F. Melani, M. Montali, C. Martini, C. Ghelardini, M. Norcini, and A. Costanzo J. Med. Chem. 52 2009 4668
42. A. Costanzo, G. Guerrini, G. Ciciani, F. Bruni, C. Costagli, S. Selleri, B. Costa, C. Martini, and P. Malmberg-Aiello Med. Chem. Res. 11 2002 87
43. A. Costanzo, G. Guerrini, F. Bruni, and S. Selleri J. Heterocycl. Chem. 31 1994 1369
44. H. Le Deit, S. Cron, and M. Le Corre Tetrahedron Lett. 32 1991 2759
45. G. Guerrini, G. Ciciani, F. Bruni, S. Selleri, C. Martini, S. Daniele, C. Ghelardini, L. Di Cesare Mannelli, and A. Costanzo Bioorg. Med. Chem. 19 2011 7441
46. A. Costanzo, G. Guerrini, G. Ciciani, F. Bruni, S. Selleri, B. Costa, C. Martini, A. Lucacchini, P. Malmberg-Aiello, and A. Ipponi J. Med. Chem. 42 1999 2218
47. M.R. Del Giudice, C. Mustazza, A. Borioni, F. Gatta, K. Tayebati, F. Amenta, P. Tucci, and S. Pieretti Arch. Pharm. 336 2003 143
48. G. Sukhanov, and A. Lukin Chem. Heterocycl. Compd. 2005 861
49. A. Sukhanova, G. Sakovich, and G. Sukhanov Chem. Heterocycl. Compd. 2008 1368
50. Hansch, C.; Leo, A.; Hoeckman, D. Exploring QSAR, Hydrophobic, Electronic and Steric Constant; ACS Professional References Book, American Chemical Society: Washington, DC, 1995.
51. C. Martini, A. Lucacchini, G. Ronca, S. Hrelia, and C.A. Rossi J. Neurochem. 38 1982 15
52. O.H. Lowry, N.J. Rosebrough, A.L. Farr, and R.J. Randall J. Biol. Chem. 193 1951 265
53. Y. Cheng, and W.H. Prusoff Biochem. Pharmacol. 22 1973 3099
54. M.E. Jarvik, and R. Kopp Psychol. Rep. 21 1967 221
55. R. Dantzer, R.-M. Bluthe, G.F. Koob, and M. Le Moal Psychopharmacology 91 1987 363
56. M.G. Giovannini, G. Spignoli, V. Carla, and G. Pepeu Pharmacol. Res. 24 1991 395
57. G. Paxinos, and C. Watson The Rat Brain in Sterotaxic Coordinates 1982 Academic Press New York
58. G. Damsma, D.L. van Bueren, B.H.C. Westerink, and A.S. Horn Chromatographia 24 1987 827
59. CrysAlis RED Oxford Diffraction (version 171.34.41); Oxford Diffraction Ltd: Abingdon, Oxfordshire, England.
60. G.M. Sheldrick Acta Crystallogr., A 64 2007 112
61. L.J. Farrugia J. Appl. Crystallogr. 32 1999 837
62. L.J. Farrugia J. Appl. Crystallogr. 30 1997 565