Triazoloquinazolinediones as novel high affinity ligands for the benzodiazepine site of GABAA receptors

Bioorganic and Medicinal Chemistry

Volumn 19, Issue 1, 2011, Pages 111-121

  Nilsson, Jakob ^a   Gidlöf, Ritha ^a   Nielsen, Elsebet Østergaard ^b   Liljefors, Tommy ^c   Nielsen, Mogens ^c   Sterner, Olov ^a  

^a LUND UNIVERSITY   (Sweden)

^b NEUROSEARCH A S   (Denmark)

^c UNIVERSITY OF COPENHAGEN   (Denmark)

Author keywords

2 Aryl 2,6 dihydro 1,2,4 triazolo 4,3 c quinazoline 3,5 diones; Benzodiazepine binding site; GABAA receptor subtypes; GABAA receptors; Pharmacophore model

Indexed keywords

2 ([[(ETHOXYCARBONYL)AMINO]CARBONOTHIOYL]AMINO) 5 METHYLBENZOIC ACID; 4 AMINOBUTYRIC ACID A RECEPTOR; 4 CHLORO 6 METHYL 2 (METHYLSULFANYL)QUINAZOLINE; 5 BROMO 2 ([[(ETHOXYCARBONYL)AMINO]CARBONOTHIOYL]AMINO)BENZOIC ACID; 6 BROMO 2 (METHYLSULFANYL) 4 (3 NITRO 1H 1,2,4 TRIAZOL 1 YL)QUINAZOLINE; 6 BROMO 2 (METHYLSULFANYL)QUINAZOLIN 4(3H)ONE; 6 BROMO 2 THIOXO 2,3 DIHYDROQUINAZOLIN 4(1H)ONE; 6 BROMO 4 CHLORO 2 (METHYLSULFANYL)QUINAZOLINE; 6 METHYL 2 (METHYLSULFANYL)QUINAZOLIN 4(3H)ONE; 6 METHYL 2 THIOXO 2,3 DIHYDROQUINAZOLIN 4(1H)ONE; 9 BROMO 2 (2 FLUOROPHENYL) 2,6 DIHYDRO[1,2,4]TRIAZOLO[4,3 C]QUINAZOLINE 3,5 DIONE; 9 BROMO 2 (2 FLUOROPHENYL) 5 (METHYLSULFANYL)[1,2,4]TRIAZOLO[4,3 C]QUINAZOLIN 3(2H)ONE; 9 BROMO 2 (4 CHLOROPHENYL) 2,6 DIHYDRO[1,2,4]TRIAZOLO[4,3 C]QUINAZOLINE 3,5 DIONE; 9 BROMO 2 (4 CHLOROPHENYL) 5 (METHYLSULFANYL)[1,2,4] TRIAZOLO[4,3 C]QUINAZOLIN 3(2H)ONE; 9 BROMO 2 (4 METHYLPHENYL) 2,6 DIHYDRO[1,2,4]TRIAZOLO[4,3 C]QUINAZOLINE 3,5 DIONE; 9 BROMO 2 (4 METHYLPHENYL) 5 (METHYLSULFANYL)[1,2,4] TRIAZOLO[4,3 C]QUINAZOLIN 3(2H)ONE; 9 BROMO 2 PHENYL 2,6 DIHYDRO[1,2,4]TRIAZOLO[4,3 C]QUINAZOLINE 3,5 DIONE; 9 BROMO 2 PHENYL 5 (METHYLSULFANYL)[1,2,4]TRIAZOLO[4,3 C]QUINAZOLIN 3(2H)ONE; 9 METHYL 2 PHENYL 2,6 DIHYDRO[1,2,4]TRIAZOLO[4,3 C]QUINAZOLINE 3,5 DIONE; 9 METHYL 5 (METHYLTHIO) 2 PHENYL[1,2,4]TRIAZOLO[4,3 C]QUINAZOLIN 3(2H)ONE; BENZODIAZEPINE; ETHYL 1 (2 FLUOROPHENYL)HYDRAZINECARBOXYLATE; ETHYL 1 (4 CHLOROPHENYL)HYDRAZINECARBOXYLATE; ETHYL 1 (4 METHYLPHENYL)HYDRAZINECARBOXYLATE; ETHYL 1 PHENYLHYDRAZINECARBOXYLATE; ETHYL 2 [6 METHYL 2 (METHYLTHIO)QUINAZOLIN 4(3H)YLIDENE] 1 PHENYLHYDRAZINECARBOXYLATE; ETHYL 6 BROMO 4 OXO 2 THIOXO 1,4 DIHYDROQUINAZOLINE 3(2H)CARBOXYLATE; ETHYL 6 METHYL 4 OXO 2 THIOXO 1,4 DIHYDROQUINAZOLINE 3(2H)CARBOXYLATE; QUINAZOLINE DERIVATIVE; UNCLASSIFIED DRUG; UNINDEXED DRUG;

ANIMAL EXPERIMENT; ANIMAL TISSUE; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL REACTION; CROSS LINKING; DRUG BINDING SITE; DRUG DESIGN; DRUG IDENTIFICATION; DRUG RECEPTOR BINDING; DRUG STRUCTURE; DRUG SYNTHESIS; NONHUMAN; PHARMACOPHORE; PROTON NUCLEAR MAGNETIC RESONANCE; RAT;

ANIMALS; BENZODIAZEPINES; LIGANDS; MAGNETIC RESONANCE SPECTROSCOPY; MODELS, MOLECULAR; PROTEIN BINDING; QUINAZOLINES; RATS; RECEPTORS, GABA-A; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION;

RATTUS;

EID: 78650744695     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2010.11.050     Document Type: Article

References (29)

1. N. Yokoyama, B. Ritter, and A.D. Neubert J. Med. Chem. 25 1982 337
2. H. Shindo, S. Takada, S. Murata, M. Eigyo, and A. Matsushita J. Med. Chem. 32 1989 1213
3. M.S. Allen, T.J. Hagen, M.L. Trudell, P.W. Codding, P. Skolnick, and J.M. Cook J. Med. Chem. 31 1988 1854
4. M.L. Trudell, S.L. Lifer, Y.C. Tan, M.J. Martin, L. Deng, P. Skolnick, and J.M. Cook J. Med. Chem. 33 1990 2412
5. D. Catarzi, L. Cecchi, V. Colotta, F. Melani, G. Filacchioni, C. Martini, L. Giusti, and A. Lucacchini J. Med. Chem. 37 1994 2846
6. P. Albaugh, L. Marshall, J. Gregory, G. White, A. Hutchison, P. Ross, D. Gallagher, J. Tallman, M. Crago, and J. Cassella J. Med. Chem. 45 2002 5043
7. X. He, Q. Huang, C. Ma, S. Yu, R. McKernan, and J.M. Cook Drug Des. Discovery 17 2000 131
8. W. Sieghart Adv. Pharmacol. 54 2006 231
9. G.A.R. Johnston Curr. Pharm. Des. 11 2005 1867
10. R.W. Olsen, and W. Sieghart Neuropharmacology 56 2009 141
11. U. Rudolph, F. Crestani, D. Benke, I. Brunig, J.A. Benson, J.M. Fritschy, J.R. Martin, H. Bluethmann, and H. Mohler Nature 401 1999 796
12. U. Rudolph, F. Crestani, and H. Möhler Trends Pharmacol. Sci. 22 2001 188
13. W. Zhang, K.F. Koehler, P. Zhang, and J.M. Cook Drug Des. Discovery 12 1995 193
14. K. Dekermendijan, P. Kanhberg, M. Witt, O. Sterner, M. Nielsen, and T. Liljefors J. Med. Chem. 42 1999 4343
15. P. Kahnberg, E. Lager, C. Rosenberg, J. Schougaard, L. Camet, O. Sterner, E. Østergaard Nielsen, M. Nielsen, and T. Liljefors J. Med. Chem. 45 2002 4188
16. E. Lager, P. Andersson, J. Nilsson, I. Pettersson, E. Østergaard Nielsen, M. Nielsen, O. Sterner, and T. Liljefors J. Med. Chem. 49 2006 2526
17. E. Lager, J. Nilsson, E. Østergaard Nielsen, M. Nielsen, T. Liljefors, and O. Sterner Bioorg. Med. Chem. 16 2008 6936
18. J. Nilsson, E. Østergaard Nielsen, T. Liljefors, M. Nielsen, and O. Sterner Bioorg. Med. Chem. Lett. 18 2008 5713
19. X. Lin, and M. Robins J. Org. Lett. 2 2000 3497
20. P. Wenter, and S. Pitsch Helv. Chim. Acta 86 2003 3955
21. M. Wolter, A. Klapars, and S.L. Buchwald Org. Lett. 3 2001 3803
22. X. Li, J. Yu, J.R. Atack, and J.M. Cook Med. Chem. Res. 5 2004 259
23. K. Dahlén, E.A.A. Wallén, M. Grøtli, and K. Luthman J. Org. Chem. 71 2006 6863
24. M. Biel, P. Deck, A. Giannis, and H. Waldmann Chem. Eur. J. 12 2006 4121
25. J. Ruiz, E. Lete, and N. Sotomayor Tetrahedron 62 2006 6182
26. J.W. Labadie, and J.K. Stille J. Am. Chem. Soc. 105 1983 6129
27. E. Campaigne, and O.E. Yokley J. Org. Chem. 28 1963 914
28. P. Kahnberg, M. Howard, T. Liljefors, M. Nielsen, E. Østergaard Nielsen, O. Sterner, and I. Pettersson J. Mol. Graphics Modell. 23 2004 253
29. D. Bonafoux, S. Bonar, L. Christine, M. Clare, A. Donnelly, J. Guzova, N. Kishore, P. Lennon, A. Libby, S. Mathialagan, W. McGhee, S. Rouw, C. Sommers, M. Tollefson, C. Tripp, R. Weier, S. Wolfson, and Y. Min Bioorg. Med. Chem. Lett. 15 2005 2870