1-aryl-4-[(5-methoxy-1,2,3,4-tetrahydronaphthalen-1- yl)alkyl]piperazines and their analogues: Influence of the stereochemistry of the tetrahydronaphthalen-1-yl nucleus on 5-HT(1A) receptor affinity and selectivity versus α1 and D2 receptors. 51

Journal of Medicinal Chemistry

Volumn 42, Issue 3, 1999, Pages 490-496

  Perrone, Roberto ^a   Berardi, Francesco ^a   Colabufo, Nicola A ^a   Leopoldo, Marcello ^a   Tortorella, Vincenzo ^a  

^a UNIVERSITY OF BARI   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

1 ARYL 4 [(5 METHOXY 1,2,3,4 TETRAHYDRONAPHTHALEN 1 YL)ALKYL]PIPERAZINE; ALPHA 1 ADRENERGIC RECEPTOR; BUSPIRONE; DOPAMINE 2 RECEPTOR; FLESINOXAN; GUANOSINE 5' O (3 THIOTRIPHOSPHATE); N [2 [4 (2 METHOXYPHENYL) 1 PIPERAZINYL]ETHYL] N (2 PYRIDYL)CYCLOHEXANECARBOXAMIDE; N TERT BUTYL 3 [4 (2 METHOXYPHENYL) 1 PIPERAZINYL] 2 PHENYLPROPIONAMIDE; PIPERAZINE DERIVATIVE; SEROTONIN 1A RECEPTOR; SULFUR 35; UNCLASSIFIED DRUG;

ARTICLE; BINDING AFFINITY; DRUG RECEPTOR BINDING; DRUG STRUCTURE; NEUROPHARMACOLOGY; NEUROTRANSMISSION; SEROTONINERGIC SYSTEM; STEREOCHEMISTRY; STRUCTURE ACTIVITY RELATION;

ANIMALS; CHO CELLS; CRICETINAE; GAS CHROMATOGRAPHY-MASS SPECTROMETRY; HUMANS; MAGNETIC RESONANCE SPECTROSCOPY; PIPERAZINES; RADIOLIGAND ASSAY; RECEPTORS, ADRENERGIC, ALPHA-1; RECEPTORS, DOPAMINE D2; RECEPTORS, SEROTONIN; RECEPTORS, SEROTONIN, 5-HT1; STEREOISOMERISM; STRUCTURE-ACTIVITY RELATIONSHIP; TETRAHYDRONAPHTHALENES;

EID: 0033010341     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm980420n     Document Type: Article

References (21)

1. 1A receptor affinity of 1-phenyl-4-[ω-(α-or β-tetralinyl)alkyl]-piperazines. 4. J. Med. Chem. 1996, 39, 4928-4934.
2. Zifa, E.; Fillion, G. 5-Hydroxytryptamine receptors. Pharmacol. Rev. 1992, 44, 401-458.
3. Teiler, M. Cloning and functional expression of serotonin receptor subtypes. Med. Chem. Res. 1993, 3, 273-286.
4. Saudou, F.; Hen, R. 5-HT receptor subtypes: molecular and functional diversity. Med. Chem. Res. 1994, 4, 16-84.
5. Broekkamp, C. L.; Leysen, D.; Peeters, B. W.; Pinder, R. M. Prospects for improved antidepressants. J. Med. Chem. 1995, 38, 4615-4633.
6. Blier, P.; de Montigny, C. Current advances and trends in the treatment of depression. Trends Pharmacol. Sci. 1994, 15, 220-226.
7. Hamon, M. Neuropharmacology of anxiety: perspectives and prospects. Trends Pharmacol. Sci. 1994, 15, 36-39.
8. 1A/D-2 Activity of a new model of arylpiperazine: 1-aryl-4-[3-(1,2-dihydronaphthalen-4-yl)-n-propyl]piperazines.1. Synthesis and structure - activity relationships. J. Med. Chem. 1994, 37, 99-104.
9. 1A receptor of 1-aryl-4-[(1-tetralin)alkyl]piperazines. 2. J. Med. Chem. 1995, 38, 942-949.
10. 1A receptor affinity, and selectivity. 3. J. Med. Chem. 1996, 39, 3195-3202.
11. 1A receptors. J. Med. Chem. 1993, 36, 1509-1510.
12. Meyer, M. D.; Hancock, A. A.; Tietje, K.; Sippy, K. B.; Giardina, W. J.; Kerwin, J. F., Jr. Synthesis and pharmacological characterization of A-80426. a putative novel antidepressant combining α-2 antagonism with 5-HT uptake inhibition. Bioorg. Med. Chem. Lett. 1995, 5, 2287-2292.
13. 2 ligands. J. Med. Chem. 1998, 41, 3940-3947.
14. Ghislandi, V.; Vercesi, D. Scissione ottica e configurazione dell'α-cicloesilbenzilammina, dell'1,2,3,4-tetraidro-l-naftilammina e dell'1,2,3,4-tetraidro-2-naftilammina. Farmaco Ed. Sci. 1972, 26, 474-486.
15. Sarges, R.; Tretter, J. R.; Tenen, S. S.; Weissman, A. 5,8-Disubstituted 1-aminotetralins. A class of compounds with a novel profile of central nervous system activity. J. Med. Chem. 1973, 16, 1003-1011.
16. Wieland, T.; Jakobs, K. H. Measurement of receptor-stimulated guanoaine 5′-O-(γ-thio)triphoaphate binding by G proteins. In Heterotrimeric G Proteins; Iyengar, R., Ed.; Academic Press: San Diego, CA, 1994; pp 3-13.
17. 1A receptor antagonist, WAY-100635. Eur. J. Pharmacol. 1995, 281, 81-88.
18. 1A and D-2 receptor affinity of o-methoxyphenylpiperazine derivatives with terminal benzamide fragment on N-4 alkyl chain. 2. Farmaco 1995, 50, 505-510.
19. Bourdais, J. L'alcoylation des piperazines dans le N,N-dimethylformamide. Bull. Soc. Chim. Fr. 1968, 3246-3249.
20. 1A/D-2 ligands. Med. Chem. Res. 1997, 7, 76-86.
21. Lazareno, S.; Farries, T.; Birdsall, N. J. Pharmacological characterization of guanine nucleotide exchange reactions in membranes from CHO cells stably transfected with human muscarinic receptors m1-m4. Life Sci. 1993, 52, 449-456.