Binding and preliminary evaluation of 5-hydroxy- and 10-hydroxy- 2,3,12,12a-tetrahydro-1H-[1]benzoxepino[2,3,4-ij]isoquinolines as dopamine receptor ligands

Journal of Medicinal Chemistry

Volumn 43, Issue 4, 2000, Pages 599-608

  Claudi, Francesco ^a   Di Stefano, Antonio ^b   Napolitani, Fabrizio ^a   Cingolani, Gian Mario ^a   Giorgioni, Gianfabio ^a   Fontenla, Josè A ^c   Montenegro, Gisela Y ^c   Rivas, Maria E ^c   Rosa, Elizabeth ^c   Michelotto, Barbara ^b   Orlando, Giustino ^b   Brunetti, Luigi ^b  

^a UNIVERSITY OF CAMERINO   (Italy)

^b UNIVERSITY OF CHIETI   (Italy)

^c UNIVERSITY OF SANTIAGO DE COMPOSTELA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

10 HYDROXY 2,3,12,12A TETRAHYDRO 1H(1) BENZOXEPINO[2,3,4 IJ]ISOQUINOLINE; 4 BROMO 10 METHOXY 1 METHYL 2,3,12,12A TETRAHYDRO 1H(1) BENZOXEPINO[2,3,4 IJ]ISOQUINOLINE OXALIC ACID; 5 HYDROXY 2,3,12,12A TETRAHYDRO 1H(1) BENZOXEPINO[2,3,4 IJ]ISOQUINOLINE; DOPAMINE 1 RECEPTOR; DOPAMINE 2 RECEPTOR; DOPAMINE 2 RECEPTOR STIMULATING AGENT; DOPAMINE 4 RECEPTOR; DOPAMINE RECEPTOR; ISOQUINOLINE DERIVATIVE; PROLACTIN; RECEPTOR SUBTYPE; SPIPERONE; TRITIUM; UNCLASSIFIED DRUG;

ADENOHYPOPHYSIS; ANIMAL TISSUE; ARTICLE; BINDING AFFINITY; DOPAMINERGIC SYSTEM; DRUG RECEPTOR BINDING; HYPOPHYSIS CELL; LIGAND BINDING; MALE; NONHUMAN; PROLACTIN RELEASE; RAT;

ANIMALS; BINDING, COMPETITIVE; CELL LINE; CORPUS STRIATUM; DOPAMINE AGONISTS; DOPAMINE ANTAGONISTS; HUMANS; ISOQUINOLINES; LIGANDS; MALE; MODELS, MOLECULAR; PITUITARY GLAND, ANTERIOR; PROLACTIN; RADIOLIGAND ASSAY; RATS; RATS, WISTAR; RECEPTORS, DOPAMINE D1; RECEPTORS, DOPAMINE D2; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 17744402326     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm991034o     Document Type: Article

References (26)

1. 2 dopamine receptors in schizophrenia, Alzheimer's, Parkinson's, and Huntington's diseases. Neuropsychopharmacology 1987, 1, 5-15.
2. Cannon, J. C. Dopamine agonists: Structure-activity relationships. In Progress in Drug Research; Jucker, E., Ed.; Birkauser: Basel, 1985; Vol. 29, pp 303-414.
3. Iorio, L. C.; Barnett, A.; Leitz, F. H.; Houser, V. P.; Korduba, C. SCH 23390, a potential benzazepine antipsychotic with unique interactions on dopaminergic system. J. Pharmacol. Exp. Ther. 1983, 226, 462-468.
4. Kebabian, J. W.; DeNinno, M. P.; Schoenleber, R.; MacKenzie, R.; Britton, D. R.; Asin, K. E. A68930: a potent agonist specific for the dopamine DI receptor. Neurochem. Int. 1992, 20, 1575-1605.
5. 1 dopamine receptor agonists: pharmacophore assessment and receptor mapping. J. Med. Chem. 1996, 39, 285-296.
6. McDermed, J. D.; Freeman, H. S.; Ferris, R. M. Catecholamines: Basic Clinical Front. In Proc. Int. Catecholamine Symp. 4th 1978; Usdin, E., Kopin, I. J., Barchas, J., Eds.; Pergamon: New York, 1979; pp 568-570.
7. 1A receptor binding modes of the enantiomers of 5-OMe-BPAT. Bioorg. Med. Chem. 1999, 7, 1805-1820.
8. 2-like receptors. Biochem. J. 1992, 287, 277-282.
9. Hibert, M. F.; Trumpp-Kallmeyer, S.; Bruinvels, A.; Hoflack J. Three-Dimensional models of neurotransmitter G-binding protein-coupled receptors. J. Mol. Pharmacol. 1991, 40, 8-15.
10. Gao, Y.; Zong, R.; Campbell, A.; Kula, N. S.; Baldessarini, R. J.; Neumeyer, J. L. Synthesis and dopamine agonist and antagonist effects of (R)-(-)- and (S)-(+)-11-hydroxy-N-n-propylnoraporphine. J. Med. Chem. 1988, 31, 1392-1396.
11. Claudi, F.; Giorgioni, G.; Di Stefano, A.; Abbracchio, M. P.; Paoletti, A. M.; Balduini, W. Synthesis and pharmacological characterization of 2-(4-chloro-3-hydroxyphenyl)ethylamine and N,N-dialkyl derivatives as dopamine receptor ligands. J. Med. Chem. 1992, 35, 4408-4414.
12. Claudi, F.; Cingolani, G. M.; Di Stefano, A.; Giorgioni, G.; Amenta, F.; Barili, P.; Ferrari, F.; Giuliani, D. Synthesis, resolution, and preliminary evaluation of trans-2-amino-6(5)-hydroxy-1-phenyl-2,3-dihydro-1H-indenes and related derivatives as dopamine receptor ligands. J. Med. Chem. 1996, 39, 4238-4246.
13. 3H]Raclopride binding sites. Experientia 1992, 48, 27-30.
14. Kametani, T.; Shibuia, S.; Nakano, T.; Fukumoto, K. Studies on the synthesis of heterocyclic compounds. Part CDXLIII. An alternative synthesis of (±)-Glaziovine by photolysis and phenolic oxidation. J. Chem. Soc. C 1971, 3818-3821.
15. Casagrande, C.; Canonica, L. Studies on proaporphine and aporphine alkaloids. Part V. Synthesis of (±)-Glaziovine by 8,1′-ring closure of 1-benzylisoquinolines derivatives. J. Chem. Soc., Perkin Trans. 1 1975, 1647-1652.
16. 2 dopamine receptor negatively coupled with adenylate cyclase in rat anterior pituitary. Mol. Pharmacol. 1983, 23, 576-584.
17. 2 receptor mediates both inhibitory and stimulatory actions on prolactin release. Endocrine 1997, 7, 177-82.
18. 2, and agonist receptor sites in rat brain. J. Med. Chem. 1990, 33, 39-44.
19. 2 binding sites both in vitro and in vivo. Eur. J. Pharmacol. 1992, 210, 279-284.
20. Seeman, P.; Grigoriadis, D. Dopamine receptors in brain and periphery. Neurochem. Int. 1987, 10, 1-25.
21. Ben-Jonathan, N.; Arbogast, L. A.; Hyde, J. F. Neuroendocrine regulation of prolactin release. Prog. Neurobiol. 1989, 33, 399-447.
22. 2-dopamine receptor agonist, at low concentrations on prolactin release in female rats in vitro. Life Sci. 1992, 51, 727-732.
23. Fleming, I.; Woolias, M. A. New synthesis of indoles particularly suitable for the synthesis of tryptamines and tryptamine Itself. J. Chem. Soc., Perkin Trans. 1 1979, 829-837.
24. Hodgson, H. H.; Beard, H. G. Bromo-derivatives of m-hydroxybenzaldehyde. J. Chem. Soc. 1925, 875-890.
25. Keseru, G. M.; Mezey-Vandor, G.; Nogradi, M.; Vermes, B.; Kajtar-Peredy, M. Total synthesis of Plagiochins C, macrocyclic bis(bibenzyl)constituents of Plagiochila acantophylla. Tetrahedron 1992, 48, 913-922.
26. Brunetti, L.; Preziosi, P.; Ragazzoni, E.; Vacca, M.; Effects of lipopolysaccharide on hypothalamic-pituitary-adrenal axis in vitro. Life Sci. 1994, 54, 165-171.