메뉴 건너뛰기




Volumn 48, Issue 22, 2005, Pages 6855-6869

Synthesis, structure-activity relationships, and biological properties of 1-heteroaryl-4-[ω-(1H-indol-3-yl)alkyl]piperazines, novel potential antipsychotics combining potent dopamine D2 receptor antagonism with potent serotonin reuptake inhibition

Author keywords

[No Author keywords available]

Indexed keywords

8 [4 [3 (5 FLUORO 1H INDOL 3 YL)PROPYL] 1 PIPERAZINYL] 2 METHYL 1,4 BENZOXAZIN 3(4H) ONE; 8 [4 [3 (5 FLUORO 1H INDOL 3YL)PROPYL]PIPERAZIN 1 YL] 4H BENZO[1,4]OXAZIN 2 METHYL 3 ONE; BICYCLO COMPOUND; DOPAMINE 2 RECEPTOR BLOCKING AGENT; NEUROLEPTIC AGENT; PIPERAZINE DERIVATIVE; SEROTONIN TRANSPORTER; SEROTONIN UPTAKE INHIBITOR; UNCLASSIFIED DRUG;

EID: 27444437203     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm050148z     Document Type: Article
Times cited : (61)

References (49)
  • 1
    • 0032977410 scopus 로고    scopus 로고
    • The effects of clozapine, risperidone, and olanzapine on cognitive function in schizophrenia
    • Meltzer, H. Y.; McGurk, S. R. The effects of clozapine, risperidone, and olanzapine on cognitive function in schizophrenia. Schizophr. Bull. 1999, 25, 233-255.
    • (1999) Schizophr. Bull. , vol.25 , pp. 233-255
    • Meltzer, H.Y.1    McGurk, S.R.2
  • 2
    • 0342288642 scopus 로고    scopus 로고
    • The efficacy of atypical antipsychotics in the treatment of depressive symptoms, hostility, and suicidality in patients with schizophrenia
    • Keck, P. E.; Strakowski, S. M.; McCelroy, S. L. The efficacy of atypical antipsychotics in the treatment of depressive symptoms, hostility, and suicidality in patients with schizophrenia. J. Clin. Psychiatry 2000, 61, 4-9.
    • (2000) J. Clin. Psychiatry , vol.61 , pp. 4-9
    • Keck, P.E.1    Strakowski, S.M.2    McCelroy, S.L.3
  • 3
    • 0033850147 scopus 로고    scopus 로고
    • Depression in schizophrenia: Perspective in the era of 'atypical' antipsychotic agents
    • (b) Siris, S. G. Depression in schizophrenia: Perspective in the era of 'atypical' antipsychotic agents. Am. J. Psychiatry 2000, 157, 1379-1389.
    • (2000) Am. J. Psychiatry , vol.157 , pp. 1379-1389
    • Siris, S.G.1
  • 4
    • 0027275084 scopus 로고
    • Depression, demoralization and control over psychotic illness: A comparison of depressed and nondepressed patients with a chronic psychosis
    • Birchwood, M.; Mason, R.; Macmillan, F. Depression, demoralization and control over psychotic illness: A comparison of depressed and nondepressed patients with a chronic psychosis. Psychol Med. 1993, 23, 387-395.
    • (1993) Psychol. Med. , vol.23 , pp. 387-395
    • Birchwood, M.1    Mason, R.2    Macmillan, F.3
  • 5
    • 0020527777 scopus 로고
    • Depression in chronic schizophrenia
    • (b) Roy, A.; Thompson, R.; Kennedy, S. Depression in chronic schizophrenia. Br. J. Psychiatry 1983, 142, 465-470.
    • (1983) Br. J. Psychiatry , vol.142 , pp. 465-470
    • Roy, A.1    Thompson, R.2    Kennedy, S.3
  • 6
    • 0020052571 scopus 로고
    • 3H]spiroperidol binding sites in rat striatum: Evidence for pharmacologically distinct classes of receptors
    • 3H]spiroperidol binding sites in rat striatum: Evidence for pharmacologically distinct classes of receptors. Brain Res. 1982, 235, 205-211.
    • (1982) Brain Res. , vol.235 , pp. 205-211
    • Rosenfeld, M.R.1    Dvorkin, B.2    Klein, P.N.3    Makman, M.H.4
  • 8
    • 0017842293 scopus 로고
    • Mechanism of the anti-psychotic effect in the treatment of acute schizophrenia
    • (c) Johnstone, E. C.; Crow, T. J.; Frith, C. D.; Carney, M. W.; Price, J. S. Mechanism of the anti-psychotic effect in the treatment of acute schizophrenia. Lancet 1978, 8069, 848-851.
    • (1978) Lancet , vol.8069 , pp. 848-851
    • Johnstone, E.C.1    Crow, T.J.2    Frith, C.D.3    Carney, M.W.4    Price, J.S.5
  • 9
    • 0019174607 scopus 로고
    • Relationship of neuroleptic drug effects at brain dopamine, serotonin, alpha-adrenergic, and histamine receptors to clinical potency
    • (d) Peroutka, S. J.; Snyder, S. H. Relationship of neuroleptic drug effects at brain dopamine, serotonin, alpha-adrenergic, and histamine receptors to clinical potency. Am. J. Psychiatry 1980, 137, 1518-1522.
    • (1980) Am. J. Psychiatry , vol.137 , pp. 1518-1522
    • Peroutka, S.J.1    Snyder, S.H.2
  • 10
    • 0017255979 scopus 로고
    • Dopamine receptor binding predicts clinical and pharmacological potencies of antischizophrenic drugs
    • Creese, I.; Burt, D. R.; Snyder, S. H. Dopamine receptor binding predicts clinical and pharmacological potencies of antischizophrenic drugs. Science 1976, 192, 481-483.
    • (1976) Science , vol.192 , pp. 481-483
    • Creese, I.1    Burt, D.R.2    Snyder, S.H.3
  • 11
    • 0017068246 scopus 로고
    • Antipsychotic drug doses and neuroleptic/dopamine receptors
    • (b) Seeman, P.; Lee, T.; Chau-Wong, M.; Wong, K. Antipsychotic drug doses and neuroleptic/dopamine receptors. Nature 1976, 261, 717-719.
    • (1976) Nature , vol.261 , pp. 717-719
    • Seeman, P.1    Lee, T.2    Chau-Wong, M.3    Wong, K.4
  • 13
    • 0032868798 scopus 로고    scopus 로고
    • The role of serotonin in antipsychotic drug action
    • Meltzer, H. The role of serotonin in antipsychotic drug action. Neuropsychopharmacology 1999, 21, 106S-115S.
    • (1999) Neuropsychopharmacology , vol.21
    • Meltzer, H.1
  • 14
    • 0033845691 scopus 로고    scopus 로고
    • Fluvoxamine augmentation of antipsychotics improves negative symptoms in psychotic chronic Schizophrenic patients: A placebo-controlled study
    • Silver, H.; Barash, I.; Aharon, N.; Kaplan, A.; Poyurovsky, M. Fluvoxamine augmentation of antipsychotics improves negative symptoms in psychotic chronic Schizophrenic patients: A placebo-controlled study. Int. Clin. Psychopharmacol. 2000, 15, 257-261.
    • (2000) Int. Clin. Psychopharmacol. , vol.15 , pp. 257-261
    • Silver, H.1    Barash, I.2    Aharon, N.3    Kaplan, A.4    Poyurovsky, M.5
  • 16
    • 0028914983 scopus 로고
    • A placebo-controlled trial of fluoxetine added to neuroleptic in patients with schizophrenia
    • (b) Goff, D. C.; Midha, K. K.; Sarid-Segal, O.; Hubbard, J. W.; Amico, E. A placebo-controlled trial of fluoxetine added to neuroleptic in patients with schizophrenia. Psychopharmacology 1995, 117, 417-423.
    • (1995) Psychopharmacology , vol.117 , pp. 417-423
    • Goff, D.C.1    Midha, K.K.2    Sarid-Segal, O.3    Hubbard, J.W.4    Amico, E.5
  • 17
    • 0029903904 scopus 로고    scopus 로고
    • Fluoxetine augementation of clozapine treatment in patients with schizophrenia
    • (c) Buchanan, R. W.; Kirkpatrick, B.; Bryant, N.; Ball, P.; Breier, A. Fluoxetine augementation of clozapine treatment in patients with schizophrenia. Am. J. Psychiatry 1996, 153, 1625-1627.
    • (1996) Am. J. Psychiatry , vol.153 , pp. 1625-1627
    • Buchanan, R.W.1    Kirkpatrick, B.2    Bryant, N.3    Ball, P.4    Breier, A.5
  • 20
    • 0031803116 scopus 로고    scopus 로고
    • Augmentation with fluvoxamine but not maprotiline improves negative symptoms in treated Schizophrenia: Evidence for a specific serotonergic effect from a double-blind study
    • Silver, H.; Shmugliakov, N. Augmentation with fluvoxamine but not maprotiline improves negative symptoms in treated Schizophrenia: Evidence for a specific serotonergic effect from a double-blind study. J. Clin. Psychopharmacol. 1998, 18, 208-211.
    • (1998) J. Clin. Psychopharmacol. , vol.18 , pp. 208-211
    • Silver, H.1    Shmugliakov, N.2
  • 25
    • 0004268476 scopus 로고
    • Compounds 6, m = 2 and m = 3, are commercially available. Compound 6, m = 4, can be prepared as described in Frits, H. E. J. Org. Chem, 1963, 28, 1384-1386.
    • (1963) J. Org. Chem. , vol.28 , pp. 1384-1386
    • Frits, H.E.1
  • 26
    • 0031523832 scopus 로고    scopus 로고
    • Process development of 5-fluoro-3-[3-[4-(5-methoxy-4pyrimidinyl)-1- piperazinyl]propyl]-1H-indole-dihydrochloride
    • Anderson, N. G.; Winter, W. J.; et al. Process development of 5-fluoro-3-[3-[4-(5-methoxy-4pyrimidinyl)-1-piperazinyl]propyl] -1H-indole-dihydrochloride. Org. Process Res. Dev. 1997, 1, 300-210.
    • (1997) Org. Process Res. Dev. , vol.1 , pp. 300-1210
    • Anderson, N.G.1    Winter, W.J.2
  • 28
    • 0039914406 scopus 로고
    • Formylation of amines
    • Huffman, C. W. Formylation of amines. J. Org. Chem. 1958, 23, 727-729.
    • (1958) J. Org. Chem. , vol.23 , pp. 727-729
    • Huffman, C.W.1
  • 30
    • 0034692414 scopus 로고    scopus 로고
    • Beckmann rearrangement of 1-indanone oxim derivatives using aluminium chloride and mechanistic considerations
    • Lee, B. S.; Chu, S.; Lee, I. Y.; Lee, B.-S.; EuiSong, C.; Chi, D. Y. Beckmann rearrangement of 1-indanone oxim derivatives using aluminium chloride and mechanistic considerations. Bull. Korean Chem. Soc. 2000, 21 (9), 860-866.
    • (2000) Bull. Korean Chem. Soc. , vol.21 , Issue.9 , pp. 860-866
    • Lee, B.S.1    Chu, S.2    Lee, I.Y.3    Lee, B.-S.4    Euisong, C.5    Chi, D.Y.6
  • 31
    • 37049130646 scopus 로고
    • The Schmidt reaction with benzocycloalkenones
    • Tomita, M.; Minami, S.; Uyeo, S. The Schmidt reaction with benzocycloalkenones. J. Chem. Soc. (C) 1969, 183-189.
    • (1969) J. Chem. Soc. (C) , pp. 183-189
    • Tomita, M.1    Minami, S.2    Uyeo, S.3
  • 36
    • 0018227116 scopus 로고
    • Climbing behaviour induced by apomorphine in mice: A potential model for the detection of neuroleptic activity
    • Costall, B.; Naylor, R. J.; Nohria, V. Climbing behaviour induced by apomorphine in mice: A potential model for the detection of neuroleptic activity. Eur. J. Pharmacol. 1978, 1, 39-50.
    • (1978) Eur. J. Pharmacol. , vol.1 , pp. 39-50
    • Costall, B.1    Naylor, R.J.2    Nohria, V.3
  • 37
    • 0017086367 scopus 로고
    • An animal behavior model for studying central serotonergic synapses
    • Jacobs, B. L. An animal behavior model for studying central serotonergic synapses. Life Sci. 1976, 19 (6), 777-785.
    • (1976) Life Sci. , vol.19 , Issue.6 , pp. 777-785
    • Jacobs, B.L.1
  • 39
    • 0036489463 scopus 로고    scopus 로고
    • Molecular design based on 3D-pharmacophore. Application on 5-HT subtypes receptors
    • Bureau, R.; Daveu, C.; Lancelot, J.-C.; Rault, S. Molecular design based on 3D-pharmacophore. Application on 5-HT subtypes receptors. J. Chem. Inf. Comput. Sci. 2002, 42, 429-436.
    • (2002) J. Chem. Inf. Comput. Sci. , vol.42 , pp. 429-436
    • Bureau, R.1    Daveu, C.2    Lancelot, J.-C.3    Rault, S.4
  • 40
    • 27444445675 scopus 로고    scopus 로고
    • Internal communication, unpublished results
    • Tipker, J. Internal communication, unpublished results.
    • Tipker, J.1
  • 41
    • 0000545733 scopus 로고
    • Conformational analysis of 1-arylpiperazines and 4-arylpiperidines
    • Dijkstra, G. D. H. Conformational analysis of 1-arylpiperazines and 4-arylpiperidines. Recl. Trav. Chim. Pays-Bas 1993, 112, 151-160.
    • (1993) Recl. Trav. Chim. Pays-Bas , vol.112 , pp. 151-160
    • Dijkstra, G.D.H.1
  • 43
    • 27444443867 scopus 로고    scopus 로고
    • note
    • The lowest energy conformation that was found had an h.o.f. of 11.4 kcal/mol.
  • 44
    • 3242794178 scopus 로고    scopus 로고
    • From magic bullets to designed multiple ligands
    • Morphy, R.; Kay, C.; Rankovic, Z. From magic bullets to designed multiple ligands. Drug Discuss. Today 2004, 9, 641-651.
    • (2004) Drug Discuss. Today , vol.9 , pp. 641-651
    • Morphy, R.1    Kay, C.2    Rankovic, Z.3
  • 45
    • 0029892497 scopus 로고    scopus 로고
    • P-Glycoprotein in the blood-brain barrier of mice influences the brain penetration and pharmacological activity of many drugs
    • Schinkel, A. H.; Wagenaar, E.; Mol, C. A. A. M.; van Deemter, L. P-Glycoprotein in the blood-brain barrier of mice influences the brain penetration and pharmacological activity of many drugs. J. Clin. Invest. 1996, 97 (11), 2517-2524.
    • (1996) J. Clin. Invest. , vol.97 , Issue.11 , pp. 2517-2524
    • Schinkel, A.H.1    Wagenaar, E.2    Mol, C.A.A.M.3    Van Deemter, L.4
  • 46
    • 0028825399 scopus 로고
    • Absence of the mdr1a P-glycoprotein in mice affects tissue distribution and pharmacokinetics of dexamethasone, digoxin and cyclosporin A
    • (b) Schinkel, A. H.; Wagenaar, E.; van Deemter, L.; Mol, C. A. A. M.; Borst, P. Absence of the mdr1a P-glycoprotein in mice affects tissue distribution and pharmacokinetics of dexamethasone, digoxin and cyclosporin A. J. Clin. Invest. 1995, 96, 1698-1705.
    • (1995) J. Clin. Invest. , vol.96 , pp. 1698-1705
    • Schinkel, A.H.1    Wagenaar, E.2    Van Deemter, L.3    Mol, C.A.A.M.4    Borst, P.5
  • 48
    • 27444445266 scopus 로고    scopus 로고
    • note
    • 2 receptor in CHO cells). A pharmacological paper with more details on the in vitro and in vivo pharmacology of 45c is in preparation.
  • 49
    • 27444443672 scopus 로고    scopus 로고
    • Tripos Inc., St. Louis, MO 63144
    • Tripos Inc., St. Louis, MO 63144.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.