Preparation and pharmacological characterization of trans-2-amino-5(6)- fluoro-6(5)-hydroxy-1-phenyl-2,3-dihydro-1H-indenes as D2-like dopamine receptor agonists

Journal of Medicinal Chemistry

Volumn 48, Issue 7, 2005, Pages 2646-2654

  Di Stefano, Antonio ^a   Sozio, Piera ^a   Cacciatore, Ivana ^a   Cocco, Alessandra ^a   Giorgioni, Gianfabio ^b   Costa, Barbara ^c   Montali, Marina ^c   Lucacchini, Antonio ^c   Martini, Claudia ^c   Spoto, Giuseppe ^a   Di Pietrantonio, Francesco ^a   Di Matteo, Elisabetta ^a   Pinnen, Francesco ^a  

^a UNIVERSITY OF CHIETI   (Italy)

^b UNIVERSITY OF CAMERINO   (Italy)

^c UNIVERSITY OF PISA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

2 AMINO 5(6) FLUORO 6(5) HYDROXY 1 PHENYL 2,3 DIHYDRO 1H INDENE; 8 CHLORO 2,3,4,5 TETRAHYDRO 3 METHYL 5 PHENYL 1H 3 BENZAZEPIN 7 OL HYDROGEN MALEATE; ADENYLATE CYCLASE; CATECHOL METHYLTRANSFERASE; CYCLIC GMP; DOPAMINE 2 RECEPTOR STIMULATING AGENT; EMONAPRIDE; UNCLASSIFIED DRUG;

ARTICLE; BIOAVAILABILITY; CORPUS STRIATUM; DOPAMINERGIC TRANSMISSION; DRUG SYNTHESIS; ENZYME ACTIVITY; ENZYME DEGRADATION; MOLECULAR CLONING; NUCLEAR OVERHAUSER EFFECT; RECEPTOR AFFINITY; SCHIZOPHRENIA; SOLUBILITY;

ANIMALS; BINDING, COMPETITIVE; CORPUS STRIATUM; CYCLIC AMP; CYCLIC GMP; INDENES; RADIOLIGAND ASSAY; RATS; RECEPTORS, DOPAMINE D2; STRUCTURE-ACTIVITY RELATIONSHIP; SWINE;

EID: 20244377229     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm040889k     Document Type: Article

References (26)

1. Jackson, D. M.; Westlind-Danielsson, A. Dopamine receptors: molecular biology, biochemistry and behavioural aspects. Pharmacol. Ther. 1994, 64, 291-370.
2. 2 dopamine receptors in schizophrenia, Alzheimer's, Parkinson's and Huntington's diseases. Neuropsycopharmacology 1987, 1, 5-15.
3. Missale, C.; Nash, S. R.; Robinson, S.; Jaber, M.; Caron, M. G. Dopamine receptors: from structure to function. Physiol. Rev. 1998, 78, 189-225.
4. Nedelec, L.; Dumont, C.; Oberlander, C.; Frechet, D.; Luarent, J.; Boisier, J. R. Synthèse et étude de l'activité dopaminergique de dérivés de la di-(phényléthl)amine (Synthesis and study of the activity of dopamine derivatives of diphenylethylamine). Eur. J. Med. Chem.-Chim. Ther. 1978, 13, 553-563.
5. 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-amino-6(5)-hydroxy-1-phenyl-2,3-dihydro-1H-indenes and related derivatives as dopamine receptors ligands. J. Med. Chem. 1998, 39, 4238-4246.
6. 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.
7. Claudi, F.; Giorgioni, G.; Di Stefano, A.; Abbracchio, M. P.; Paoletti, A. M.; Balduini, W. Synthesis and pharmacological characterization of 2-(4-cloro-3-hydroxyphenyl)ethylamine and N,N-dialkyl derivatives as dopamine receptor ligands. J. Med. Chem. 1932, 35, 4408-4414.
8. Weinstock, J.; Gaitanopoulos, D. E.; Oh, H. J.; Pfeiffer, F. R.; Karash, C. B.; Venslavsky, J. W. H.; Sarau, M.; Flaim, K. E.; Hielbe, J. P.; Kaiser, K. Synthesis and dopaminergic activity of some halogenated mono- and dihydroxylated 2-aminotetralins. J. Med. Chem. 1986, 29, 1615-1627.
9. Claudi, F.; Cardellini, M.; Cingolani, G. M.; Piergentili, A.; Peruzzi, G.; Balduini, W. Synthesis and dopamine receptor affinities of 2-(4-fluoro-3-hydroxyphenyl)ethylamine and N-substituted derivatives. J. Med. Chem. 1980, 33, 2408-2412.
10. Kozlik, A.; Jeremy, S. B.; Lesley, N. P. Boots Co. PLC, U.K. Substituted tetrahydroisoquinolines and their use as therapeutic agents, WO 13073. Expert Opin. Ther. Pat. 1994, 4, 1493-1507.
11. Di Stefano, A.; Sozio, P.; Luisi, G.; Cacciatore, I.; Mosciatti, B.; Costa, B.; Lucacchini, A.; Martini, C.; Pinnen, F. Synthesis and preliminary pharmacological evaluation of trans-2-amino-5(6)-chloro-6(5)-hydroxy-1-phenyl-2, 3-dihydro-1H-indenes as dopamine receptor ligands. Farmaco 2002, 57, 303-313.
12. Gao, Y.; Ram, V. J.; Campbell, A.; Kula, N. S.; Baldessarini, R. J.; Neumeyer, J. L. Synthesis and structural requirements of N-substituted norapomorphines for affinity and activity at dopamine D1, D2 and agonist receptor sites in rat brain. J. Med. Chem. 1980, 33, 39-44.
13. Stavber, S.; Jereb, M.; Zupan, M. Solvent directed immediate fluorination of aromatic chetones using 1-fluoro-4-hydroxy-1,4-diazoniabicclo[2.2.2]octane bis(tetrafluoroborate). Chem. Commun. 2000, 14, 1323-1324.
14. Ryoji, K.; Akihiro, T.; Fukami, H.; Egawa, M. Synthesis and antianxiety activity of (ω-piperazinylalkoxy)indan derivatives. J. Med. Chem. 1983, 26, 246-250.
15. Laus, G.; Tourwé, D.; Van Bist, G. Benzo- and indoloquinolizidine derivatives XIX. The synthesis and pharmacological activity of some derivatives, analogues of butaclamol. Heterocycles 1984, 22, 311-331.
16. Marchini, P.; Liso, G.; Reho, A.; Liberatore, F.; Micheletti Moracci, F. Sodium borohydride-carboxylic acid systems. Useful reagents for the alkylation of amines. J. Org. Chem. 1975, 40, 3453-3456.
17. Fujii, N.; Irie, H.; Yajima, H. Regioselective cleavage of aromatic methyl ethers by methanesulphonic acid in the presence of methionine. J. Chem. Soc., Perkin Trans. 1 1977, 2288-2289.
18. 2 dopamine receptor subtypes in the in vivo control of neostriatal cyclic GMP. Eur. J. Pharmacol. 1990, 181, 17-21.
19. Spoto, G.; Fioroni, M.; Rubini, C.; Contente, A.; Di Nicola, M. Cyclic guanosine monophosphate phosphodiesterase activity in human gingival carcinoma. J. Oral Pathol. Med. 2003, 32, 189-194.
20. Spoto, G.; Whitehead, E.; Ferraro, A.; Di Terlizi, P. M.; Turano, C.; Riva, F. A reverse-phase HPLC method for cAMP phosphodiesterase activity. Anal. Biochem. 1991, 196, 207-210.
21. 2 dopamine receptors in rat limbocortical areas. II. Dorsal hippocampus. Neurosci. Lett. 1988, 87, 253-258.
22. Euvrard, C.; Ferland, L.; Di Paolo, T.; Beaulieu, M.; Labrie, F.; Oberlander, C.; Raynaud, J. P.; Boissier, J. R. Activity of two new potent dopaminergic agonists at the striatal and anterior pituitary levels. Neuropharmacology 1980, 19, 379-386.
23. Onali, P. L.; Olianas, M. C.; Gessa, G. L. Characterization of dopamine receptors mediating inhibition of adenylate cyclase activity in rat striatum. Mol. Pharmacol. 1985, 28, 138-145.
24. Campiani, G.; Nacci, V.; Bechelli, S. M.; Ciani, S.; Garolfo, A.; Fiorini, I.; Wikstrom, H.; de Boer, P.; Liao, Y.; Tepper, P. G.; Cagnotto, A.; Mennini, T. New antipsychotic agents with serotonin and dopamine antagonist properties based on a pyrrolo-[2,1-b][1,3]benzothiazepine structure. J. Med. Chem. 1998, 41, 3763-3772.
25. 50) of an enzymatic reaction. Biochem. Pharmacol. 1973, 22, 3099-3108.
26. Lowry, O. H.; Rosenbrough, N. J.; Farr, A. L.; Randall, R. J. Protein measurement with the folin reagent. J. Biol. Chem. 1951, 193, 265-275.