Design, synthesis and biological evaluation of new 3-[(4-aryl)piperazin- 1-yl]-1-arylpropane derivatives as potential antidepressants with a dual mode of action: Serotonin reuptake inhibition and 5-HT(1A) receptor antagonism

Farmaco

Volumn 55, Issue 5, 2000, Pages 345-353

  Oficialdegui, A M ^a   Martinez, J ^a   Perez S ^a   Heras, B ^a   Irurzun, M ^a   Palop, J A ^a   Tordera, R ^b   Lasheras, B ^b   Del Rio J ^b   Monge, A ^a  

^a Ctro Invest Farmacobiologia A   (Spain)

^b UNIVERSITY OF NAVARRA   (Spain)

Author keywords

5 HT reuptake inhibitor; 5 HT(1A) antagonist; Antidepressant; Arylpiperazine

Indexed keywords

3 [(4)PIPERAZIN 1 YL] 1 PROPANE DERIVATIVE; ANTIDEPRESSANT AGENT; ARYLPROPIONIC ACID DERIVATIVE; SEROTONIN 1A ANTAGONIST; SEROTONIN UPTAKE INHIBITOR; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ARTICLE; DRUG DESIGN; DRUG MECHANISM; DRUG RECEPTOR BINDING; DRUG STRUCTURE; DRUG SYNTHESIS; MALE; MOUSE; NONHUMAN; RAT; STRUCTURE ACTIVITY RELATION;

ANIMALS; ANTIDEPRESSIVE AGENTS; EVALUATION STUDIES; MALE; MICE; PIPERAZINES; RATS; RECEPTORS, SEROTONIN; RECEPTORS, SEROTONIN, 5-HT1; SEROTONIN UPTAKE INHIBITORS;

EID: 0033850658     PISSN: 0014827X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0014-827X(00)00050-1     Document Type: Article

References (42)

1. Stahl S.M. Mixed depression and anxiety: serotonin 1A receptor as a common pharmacological link. J. Clin. Psychiatry. 58:1997;20-26.
2. Heisser J.F., Wilcox C.S. Serotonin 5-HT1A receptor agonists as antidepressants. CNS Drugs. 10:1998;343-353.
3. Asberg M., Eriksson B., Matenson B., Traskman-Bendz L., Wagner A. Therapeutic effects of serotonin uptake inhibitors in depression. J. Clin. Psychiatry. 47:1986;23-35.
4. De Montigny C., Chaput I., Blier P. Classical and novel targets for antidepressant drugs: new pharmacological approaches to the therapy of depressive disorders. Int. Acad. Biomed. Drug Res. 5:1993;8-17.
5. Labbate L.A., Grimes J.B., Arana G.W. Serotonin reuptake antidepressant effects on sexual function in patients with anxiety disorders. Biol. Psychiatry. 43:1998;904-907.
6. Rutter J.J., Gundlah C., Auerbach S.B. Systemic uptake inhibition decreases serotonin release via somatodendritic autoreceptor activation. Synapse. 20:1995;225-233.
7. Chaput Y., De Montygny C., Blier P. Effects of a selective 5-HT reuptake blocker, citalopram, on the sensitivity of 5-HT autoreceptors: electrophysiological studies in the rat brain. Naunyn Schmiedebergs Arch. Pharmacol. 333:1986;342-348.
8. 1A autoreceptor blockade potenciates the ability of the 5-HT uptake inhibitor citalopram to increase nerve terminal output of 5-HT in vivo: a microdialysis study. J. Neurochem. 60:1993;776-779.
9. 1A receptor antagonist and an SSRIs in vivo: effects on 5-HT cell firing and extracellular 5-HT. Br. J. Pharmacol. 115:1995;1064-1070.
10. 1A receptors. Neurochem. Res. 21:1996;557-562.
11. 1A and 5-HT1B receptor antagonists on extracellular 5-HT in rat frontal cortex in vivo. Br. J. Pharmacol. 121:1997;941-946.
12. Artigas F., Perez V., Alvarez E. Pindolol induces a rapid improvement of depressed patients treated with serotonin reuptake inhibitors. Arch. Gen. Psychiatry. 51:1994;248-251.
13. Tome M.B., Cloninger C.R., Watson J.P., Isaac M.T. Serotonergic autoreceptor blockade in the reduction of antidepressant latency: personality variables and response to paroxetine and pindolol. J. Affect. Disord. 44:1997;101-109.
14. Perez V., Gilaberte I., Faries D., Alvarez E., Artigas F. Randomised, double blind, placebo-controlled trial of pindolol in combination with fluoxetine antidepressant treatment. Lancet. 349:1997;1594-1597.
15. Zanardi R., Artigas F., Franchini L., Sforzini L., Gasperini M., Smeraldi E., Perez J. How long pindolol should be associated to paroxetine to improve the antidepressant response? J. Clin. Psychopharmacol. 17:1997;446-450.
16. Puzantian T., Kawase K. Does the addition of pindolol accelerate or enhance the response to selective serotonin reuptake inhibitor antidepressants? Pharmacotherapy. 19:1999;205-212.
17. Perez V., Soler J., Puigdemont D., Alvarez E., Artigas F. A double-blind, randomized, placebo-controlled trial of pindolol augmentation in depressive patients resistant to serotonin reuptake inhibitors. Arch. Gen. Psychiatry. 56:1999;375-379.
18. Pinder R.M., Wieringa J.H. Third generation antidepressants. Med. Res. Rev. 13:1993;259-325.
19. 1A serotonin agonists and antagonist. Drug Dev. Res. 26:1992;251-274.
20. A. Monge Vega, J. del Rio Zambrana, B. Lasheras, J.A. Palop, A. Bosch, J.C. del Castillo, J. Roca. (Vita Elan Farma) WO 9902516A1.
21. Rupp A., Beuerle K.A.G., Ruf C., Folkers G. A new pharmacophoric model for 5-Ht reuptake inhibitors: differentiation of amphetamine analogues. Pharm. Acta Helv. 68:1994;235-244.
22. Bill. Knight D.J., Forster E.A., Fletcher A. Direct evidence for an important species difference in the mechanism of 8-OH-DPAT-induced hypothermia. Br. J. Pharmacol. 103:1991;1857-1864.
23. Willner P. Animal models of depression: validity and applications. Gessa G., Fratta L, Pani L., y Serra G. Depression and mania: From Neurobiology to Treatment. 1995;19-41 Raven, New York.
24. 3H-paroxetine binding to rat cortical membranes. Eur. J. Pharmacol. 118:1989;107-114.
25. 3H-ketanserine. Eur. J. Pharmacol. 118:1985;13-23.
26. 3H]-serotonin binding sites in rat and bovine brain tissue. Drug Dev. Res. 26:1992;225-234.
27. 2 receptor binding sites and functional correlates. Neuropharmacology. 23:1984;1493-1501.
28. 3 binding sites in rat brain cortical membranes. Biochem. Pharmacol. 38:1980;1693-1695.
29. Leysen J.E., Goumeren W., Laduron P.M. Spiperone: a ligand of choice for neuroleptic receptors: kinetics and characteristics of in vitro binding. Biochem. Pharmacol. 27:1978;307-316.
30. 2-adrenergic drugs also bind with high affinity to a non-adrenergic site. Mol. Pharmacol. 35:1989;324-330.
31. 2-adrenoceptor occupancy in vivo. Eur. J. Pharmacol. 212:1992;109-111.
32. Bylund D.H., Snyder S.H. Adrenergic receptor binding in membrane preparations from mammalian brain. Mol. Pharmacol. 12:1976;568-580.
33. Norman A.B., Eubanks J.H., Creese I. Irreversible and quaternary muscarinic antagonists discriminate multiple muscarinic receptor binding sites in rat brain. J. Pharmacol. Exp. Ther. 248:1989;1116-1122.
34. Porsolt R.D., Pichon L.M., Jalfre M. Depression: a new animal model sensitive to antidepressant treatments. Nature. 266:1977;730-732.
35. 3 receptor antagonists reverse helpless behaviour in rats. Eur. J. Pharmacol. 212:1992;73-78.
36. Borsini F. Role of the serotonergic system in the forced swimming test. Neurosci. Biobehav. Rev. 19:1995;377-395.
37. Luscombe G.P., Martin K.F., Hutchins L.J., Gosden J., Heal D.J. Mediation of the antidepressant-like effect of 8-OH-DPAT in mice by postsynaptic 5-HT receptors. Br. J. Pharmacol. 108:1993;669-677.
38. 1A autoreceptors and alpha 1-adrenoceptors in the inhibition of 5-HT release - I. BMY7378 and prazosin. Neuropharmacology. 34:1995;615-620.
39. 1A autoreceptors and alpha 1-adrenoceptors in the modulation of 5-HT release - III. Clozapine and the novel putative antipsychotic S 16924. Neuropharmacology. 37:1998;349-356.
40. Johansson L., Sohn D., Thorberg S.O., Jackson D.M., Kelder D., Larsson L.G., Renyi L., Ross S.B., Wallsten C., Eriksson H., Hu P.S., Jerning E., Mohell N., Westlind-Danielsson A. The pharmacological characterization of a novel selective 5-hydroxytryptamine1A receptor antagonist, NAD-299. J. Pharmacol. Exp. Ther. 283:1997;216-225.
41. Keis N.A. Cardiotoxic side effects associated with tricyclic antidepressant overdose. AACN Clin. Issues Crit. Care-Nurs. 3:1992;226-232.
42. 1A receptors in the median raphe nucleus and dorsal hippocampus may mediate anxiolytic and anxiogenic behaviours, respectively. Eur. J. Pharmacol. 264:1994;259-264.