Synthesis and binding activity of some pyrazolo[1,5-c]quinazolines as tools to verify an optional binding site of a benzodiazepine receptor ligand

Journal of Medicinal Chemistry

Volumn 39, Issue 15, 1996, Pages 2915-2921

  Colotta, Vittoria ^a   Catarzi, Daniela ^a   Varano, Flavia ^a   Filacchioni, Guido ^a   Cecchi, Lucia ^a   Galli, Alessandro ^a   Costagli, Chiara ^a  

^a UNIVERSITY OF FLORENCE   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

4 AMINOBUTYRIC ACID; BENZODIAZEPINE RECEPTOR; BETA CARBOLINE 3 CARBOXYLIC ACID ETHYL ESTER; DIAZEPAM; FLUMAZENIL; HETEROCYCLIC COMPOUND; LIGAND; PYRAZOLO[1,5 C]QUINAZOLIN 5 ONE DERIVATIVE; PYRAZOLONE DERIVATIVE; QUINAZOLINE DERIVATIVE; UNCLASSIFIED DRUG;

ANIMAL TISSUE; ARTICLE; DRUG EFFICACY; DRUG POTENCY; DRUG RECEPTOR BINDING; DRUG SYNTHESIS; MALE; NONHUMAN; RAT; RECEPTOR OCCUPANCY; STRUCTURE ACTIVITY RELATION; SYNAPTIC MEMBRANE;

ANIMALS; BINDING SITES; FLUNITRAZEPAM; HYDROGEN BONDING; MALE; PYRAZOLES; QUINAZOLINES; RATS; RATS, SPRAGUE-DAWLEY; RECEPTORS, GABA-A; STRUCTURE-ACTIVITY RELATIONSHIP; TRITIUM;

EID: 0029954302     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm9509206     Document Type: Article

References (33)

1. Haefely, W. The GABA-benzodiazepine interaction fifteen years later. Neurochem. Res. 1990, 2, 169-174.
2. Villar, H. O.; Davies, M. F.; Loew, G. H.; Maguire, P. A. Molecular models for recognition and activation at the benzodiazepine receptor: a review. Life Sci. 1991, 48, 593-602.
3. Crippen, G. M. Geometry analysis of the benzodiazepine binding site. Mol. Pharmacol. 1982, 22, 11-19.
4. Tebib, S.; Bourguignon, J. J.; Wermuth, C. G. The active analog approach applied to the pharmacophore identification of benzodiazepine receptor ligands. J. Comput.-Aided Mol. Des. 1987, 1, 153-170.
5. Villar, H. O.; Uyeno, E. T.; Toll, L.; Polgar, W.; Davies, M. F.; Loew, G. H. Molecular determinants of benzodiazepine receptor affinities and convulsant activities. Mol. Pharmacol. 1989, 36, 589-600.
6. Allen, M. S.; Tan, Y.-C.; Trudell, M. L.; Narayanan, K.; Schindler, L. R.; Martin, M. J.; Schultz, C.; Hagen, T. J.; Koehler, K. F.; Codding, P. W.; Skolnick, P.; Cook, J. M. Synthesis and computer assisted analyses of the pharmacophore for the benzodiazepine receptor inverse agonist site. J. Med. Chem. 1990, 33, 2343-2357.
7. Trudell, M. L.; Lifer, S. L.; Tan, Y.-C.; Martin, M. J.; Deng, L.; Skolnick, P.; Cook, J. M. Synthesis of substituted 7,12-dihydropyrido[3,2-b:5,4-b′]diindoles: rigid planar benzodiazepine receptor ligands with inverse agonist/antagonist properties. J. Med. Chem. 1990, 33, 2412-2420.
8. Diaz-Arauzo, H.; Koehler, K. F.; Hagen, T. J.; Cook, J. M. Synthetic and computer assisted analysis of the pharmacophore for agonists at benzodiazepine receptors. Life Sci. 1991, 49, 207-216.
9. Martin, M. J.; Trudell, M. L.; Diaz-Arauzo, H.; Allen, M. S.; LaLoggia, A. J.; Deng, L.; Schultz, C. A.; Tan, Y.-C.; Bi, Y.; Narayanan, K.; Dorn, L. J.; Koehler, K. F.; Skolnick, P.; Cook, J. M. Molecular yardsticks. Rigid probes to define the spatial dimensions of the benzodiazepine receptor binding site. J. Med. Chem. 1992, 35, 4105-4117.
10. Zhang, W.; Koehler, K. F.; Harris, B.; Skolnick, P.; Cook, J. M. Synthesis of benzo-fused benzodiazepine employed as probes of agonist pharmacophore of benzodiazepine receptors. J. Med. Chem. 1994, 37, 745-757.
11. Zhang, W.; Koehler, K. F.; Zhang, P.; Cook, J. M. Development of a comprehensive pharmacophore model for the benzodiazepine receptor. Drug Des. Discovery 1995, 12, 193-248.
12. Zhang, P.; Zhang, W.; Liu, R.; Harris, B.; Skolnick, P.; Cook, J. M. Synthesis of novel imidazobenzodiazepines as probes of the pharmacophore for diazepam-insensitive GABAA receptors. J. Med. Chem. 1995, 38, 1679-1688.
13. Colotta, V.; Catarzi, D.; Varano, F.; Melani, F.; Filacchioni, G.; Cecchi, L.; Galli, A.; Costagli, C. Benzodiazepine binding activity of some tricyclic heteroaromatic systems to define the hydrogen bonding strength of the proton donors of the receptor site. Farmaco 1996, 51, 223-229.
14. Catarzi, D.; Cecchi, L.; Colotta, V.; Filacchioni, G.; Martini, C.; Giusti, L.; Lucacchini, A.; Valle, G. Tricyclic heteroaromatic systems. 2-Phenyl-1,2,4-triazolo[1,5-c][1,3]benzoxazin-5-one: a novel benzodiazepine receptor ligand. Farmaco 1994, 49, 89-92.
15. Catarzi, D.; Cecchi, L.; Colotta, V.; Filacchioni, G.; Varano, F.; Martini, C.; Giusti, L.; Lucacchini, A. Synthesis of some 2-aryl-1,2,4-triazolo[1,5-c][1,3]benzoxazin-5-ones as tools to define the essential pharmacophoric descriptors of a benzodiazepine receptor ligand. J. Med. Chem. 1995, 38, 2196-2201.
16. Catarzi, D.; Cecchi, L.; Colotta, V.; Melani, F.; Filacchioni, G.; Martini, C.; Giusti, L.; Lucacchini, A. Structure-activity relationships of 1,2,4-triazolo[1,5-a]quinoxalines and their 1-deaza analogues imidazo[1,2-a]quinoxalines at the benzodiazepine receptor. J Med. Chem. 1994, 37, 2846-2850.
17. Colotta, V.; Cecchi, L.; Filacchioni, G.; Melani, F.; Palazzino, G.; Martini, C.; Giannaccini, G.; Lucacchini, A. Synthesis, binding activity, and structure-activity relationships of 1-aryl- and 2-aryl[1]benzopyranopyrazol-4-ones, central benzodiazepine receptor ligands. J. Med. Chem. 1988, 31, 1-3.
18. Colotta, V.; Cecchi, L.; Melani, F.; Filacchioni, G.; Martini, C.; Giannaccini, G.; Lucacchini, A. Tricyclic heteroaromatic systems. [1]Benzopyranopyrrol-4-ones and [1]benzopyrano1,2,3-triazol-4-ones as benzodiazepine receptor ligands. Synthesis and structure-activity relationships. J. Med. Chem. 1990, 33, 2646-2651.
19. Colotta, V.; Cecchi, L.; Melani, F.; Filacchioni, G.; Martini, C.; Gelli, S.; Lucacchini, A. Tricyclic heteroaromatic systems: [1]-benzopyrano-pyrazol-4-ones as benzodiazepine receptor ligands. J. Pharm. Sci. 1991, 80, 276-279.
20. Colotta, V.; Cecchi, L.; Melani, F.; Filacchioni, G.; Martini, C.; Gelli, S.; Lucacchini, A. Tricyclic heteroaromatic systems. Synthesis of 1,3- and 1,2-disubstituted[1]benzopyrano[4,3-b]pyrrol-4-ones and structure-activity relationships as benzodiazepine receptor ligands. Farmaco 1991, 46, 1139-1154.
21. Vogt, B. R. Method for treatment of asthma. U.S. patent 4,123,-532, 1978.
22. Engler, C.; Engler, A. Condensation products of α-pyridylmethylketone with benzaldehyde or o-nitrobenzaldehyde. Chem. Ber. 1902, 35, 4061-4066.
23. Barnes, R. P.; Graham, J. H.; Qureshi, M. A. S. The preparation of some benzyl-o-nitroglyoxals and cyclization of their quinoxalines. J. Org. Chem. 1963, 28, 2890-2893.
24. Ghose, A. K.; Crippen, G. M. Modeling the benzodiazepine binding site by the general three-dimentional structure-directed quantitative structure-activity relationship method REMOTE-DISC. Mol. Pharmacol. 1990, 37, 725-734.
25. Catarzi, D.; Cecchi, L.; Colotta, V.; Melani, F.; Filacchioni, G.; Martini, C.; Giusti, L.; Lucacchini, A. Tricyclic heteroaromatic systems. 1,2,4-Triazolo[1,5-a]quinoxalines: synthesis and benzodiazepine receptor activity. Farmaco 1993, 48, 1065-1078.
26. Mohler, H.; Richards, J. G. Agonist and antagonist benzodiazepine receptor interaction in vitro. Nature 1981, 294, 763-765.
27. (a) Braestrup, C.; Schmiechen, R.; Neef, G.; Nielsen, M.; Petersen, E. N. Interaction of convulsive ligands with benzodiazepine receptors. Sciences 1982, 216, 1241-1243.
28. (b) Braestrup, C.; Nielsen, M.; Honorè, T.; Jensen, L. H.; Petersen, E. N. Benzodiazepine receptor ligands with positive and negative efficacy. Neuropharmacology 1983, 22, 1451-1457.
29. (c) Braestrup, C.; Nielsen, M. Benzodiazepine receptors. In Handbook of psychopharmacology; Inversen, L. L., Inversen, S. D., Snyder, S. H., Eds.; Plenum Press: New York, 1993; Vol. 17, pp 285-384.
30. Fryer, R. I.; Rios, R.; Zhang, P.; Gu, Z.-Q.; Wong, G.; Basile, A. S.; Skolnick, P. Structure-activity relationships of 2-phenylpyrazolo[4,3-c]quinolin-3-ones and their N- and O-methyl analogues at benzodiazepine receptors. Med. Chem. Res. 1993, 3, 122-130.
31. Zukin, S. R.; Young, S. H. Gamma-aminobutyric acid binding to receptor sites in rat central nervous system. Proc. Natl. Acad. Sci. U.S.A. 1974, 71, 4802-4807.
32. De Lean, A.; Munson, P. J.; Rodbard, D. Simultaneous analysis of families of sigmoidal curves: application to bioassay, radioligand assay and physiological dose-response curves. Am. J. Physiol. 1978, 235, E97-102.
33. 50) of an enzymatic reaction. Biochem. Pharmacol. 1973, 22, 3099-3108.