Synthesis and dual D₂ and 5-HT_1A receptor binding affinities of 5-piperidinyl and 5-piperazinyl-1H-benzo[d]imidazol-2(3H)-ones

References

• Diagnostic and Statistical Manual of Mental Disorders. 4th ed. Text revision. Washington, D.C.: American Psychiatric Association; 2000:297–343
   Google Scholar
• Arnt J, Bang-Andersen B, Dias R, Bogesø KP. Strategies for pharmacotherapy of schizophrenia. Drugs Future 2008;33:777–91
   Google Scholar
• Kapur S, Agid O, Mizrahi RLM. How antipsychotics work-from receptors to reality. NeuroRx 2006;3:10–21
   PubMedGoogle Scholar
• McCormick PN, Kapur S, Graff-Guerrero A, et al. The antipsychotics olanzapine, risperidone, clozapine, and haloperidol are D2-selective ex vivo but not in vitro. Neuropsychopharmacology 2010;35:1826–35
   Google Scholar
• Meltzer HY, Li Z, Kaneda YI. Serotonin receptors: their key role in drugs to treat schizophrenia. J Prog Neuropsychopharmacol Biol Psychiatry 2003;27:1159–72
   PubMed Web of Science ®Google Scholar
• (a) Goff DC, Shader RI. Non-neurological side-effects of antipsychotic drugs. In: Hirsch SR, Weinberger D, eds. Schizophrenia. 2nd ed. Oxford: Blackwell Publishing; 2002:573–88; (b) Newman-Tancredi A, Chaput C, Verriele L, Millan MJ. Clozapine is a partial agonist at cloned, human serotonin 5-HT1A receptors. Neuropharmacology 1996;35:119–21; (c) Bartoszyk GD, Roos C, Ziegler H. 5-HT1A receptors are not involved in clozapine's lack of cataleptogenic potential. Neuropharmacology 1996;35:1645–6
   Google Scholar
• Meltzer HY. Clinical studies on the mechanism of action of clozapine: the dopamine-serotonin hypothesis of schizophrenia. Psychopharmacology 1989;99:S18–27
   PubMed Web of Science ®Google Scholar
• Lindstrom LH. The effect of long-term treatment with clozapine in schizophrenia: a retrospective study in 96 patients treated with clozapine for up to 13 years. Acta Psychiatr Scand 1988;77:524–9
   PubMed Web of Science ®Google Scholar
• Newman-Tancredi A, Cussac D, Depoortere R. Neuropharmacological profile of bifeprunox: merits and limitations in comparison with other third-generation antipsychotics. Curr Opin Investig Drugs 2007;8:539–54
   PubMed Web of Science ®Google Scholar
• Jones CA, McCreary AC. Serotonergic approaches in the development of novel antipsychotics. Neuropharmacology 2008;55:1056–65
   PubMed Web of Science ®Google Scholar
• (a) Prinssen EP, Colpaert FC, Koek W. 5-HT1A receptor activation and anti-cataleptic effects: high-efficacy agonists maximally inhibit haloperidol-induced catalepsy. Eur J Pharmacol 2002;453:217–21; (b) Depoortère R, Auclair AL, Bardin L, et al. F15063, a compound with D2/D3 antagonist, 5-HT1A agonist and D4 partial agonist properties. III. Activity in models of cognition and negative symptoms. Br J Pharmacol 2007;151:266–77
   Google Scholar
• Newman-Tancredi A, Assie MB, Leduc N, et al. Novel antipsychotics activate recombinant human and native rat serotonin 5-HT1A receptors: affinity, efficacy and potential implications for treatment of schizophrenia. Int J Neuropsychopharmacol 2005;8:341–56
   PubMed Web of Science ®Google Scholar
• Assie MB, Ravailhe V, Faucillon V, Newman-Tancredi A. Contrasting contribution of 5-hydroxytryptamine 1A receptor activation to neurochemical profile of novel antipsychotics: frontocortical dopamine and hippocampal serotonin release in rat brain. J Pharmacol Exp Ther 2005;315:265–72
   PubMed Web of Science ®Google Scholar
• Slot LAB, Vries LD, Newman-Tancredi A, Cussac D. Differential profile of antipsychotics at serotonin 5-HT1A and dopamine D2S receptors coupled to extracellular signal-regulated kinase. Eur J Pharmacol 2006;534:63–70
   Google Scholar
• Slot LAB, Kleven MS. Newman-Tancredi A. Effects of novel antipsychotics with mixed D2 antagonist/5-HT1A agonist properties on PCP-induced social interaction deficits in the rat. Neuropharmacology 2005;49:996–1006
   Google Scholar
• Kleven MS, Barret-Grevoz C, Slot LAB, Newman-Tancredi A. Novel antipsychotic agents with 5-HT1A agonist properties: role of 5-HT1A receptor activation in attenuation of catalepsy induction in rats. Neuropharmacology 2005;49:135–43
   PubMed Web of Science ®Google Scholar
• Bantick RA, Deakin JFW, Grasby PM. The 5-HT1A receptor in schizophrenia: a promising target for novel atypical neuroleptics? J Psychopharmacol 2001;15:37–46
   PubMed Web of Science ®Google Scholar
• McCreary AC, Glennon JC, Ashby Jr CR, et al. SLV313 (1-(2,3-dihydro-benzo[1,4]dioxin-5-yl)-4-[5-(4-fluoro-phenyl)-pyridin-3-ylmethyl]-piperazine monohydrochloride): a novel dopamine D2 receptor antagonist and 5-HT1A receptor agonist potential antipsychotic drug. Neuropsychopharmacology 2007;32:78–94
   Google Scholar
• Newman-Tancredi A. The importance of 5-HT1A receptor agonism in antipsychotic drug action: rationale and perspectives. Curr Opin Invest Drugs 2010;11:802–12
   PubMed Web of Science ®Google Scholar
• Cuisiat S, Bourdiol N, Lacharme V, et al. Towards a new generation of potential antipsychotic agents combining D2 and 5-HT1A receptor activities. J Med Chem 2007;50:865–76
   Google Scholar
• Ullah N. Synthesis of new 1-aryl-4-(biarylmethylene) piperazinel ligands, structurally related to adoprazine (SLV313). Z Naturforsch 2012;67b:75–84
   Google Scholar
• Ullah N, Al-Shaheri AAQ. Synthesis of new 4-aryl-1-(biarylmethylene)piperidines structural analogs of adoprazine (SLV313). Z Naturforsch 2012;67b:253–62
   Google Scholar
• Scarselli M, Novi F, Schallmach E, et al. D2/D3 dopamine receptor heterodimers exhibit unique functional properties. J Biol Chem 2001;276:30308–14
   PubMed Web of Science ®Google Scholar
• Fargin A, Raymond JR, Regan JW, et al. Effector coupling mechanisms of the cloned 5-HT1A receptor. J Biol Chem 1989;264:14848–52
   PubMed Web of Science ®Google Scholar
• Cheng Y, Prusoff WH. Relationship between the inhibition constant (Ki) and the concentration of inhibitor which causes 50 per cent inhibition (I50) of an enzymatic reaction. Biochem Pharmacol 1973;22:3099–108
   PubMed Web of Science ®Google Scholar
• Evans KM, Slawin AMZ, Lebl T, et al. An improved understanding of the reaction of bis(bromomethyl)quinoxaline 1-N-oxides with amines using substituent effects. J Org Chem 2007;72:3186–93
   Google Scholar
• Galan AA, Chen J, Du H, et al. Preparation of 1H-imidazole-4,5-dicarboxamides as JAK-2 modulators. PCT Int. Appl. 2008042282
   Google Scholar
• Pelletier JC, Chengalvala M, Cottom J, et al. 2-phenyl-4-piperazinylbenzimidazoles: orally active inhibitors of the gonadotropin releasing hormone (GnRH) receptor. Bioorg Med Chem 2008;16:6617–40
   PubMed Web of Science ®Google Scholar