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Volumn 52, Issue 15, 2009, Pages 4640-4649

Design of a new histamine H3 receptor antagonist chemotype: (3aR,6aR)-5-alkyl-1-aryl-octahydropyrrolo[3,4-b]pyrroles, synthesis, and structure-activity relationships

Author keywords

[No Author keywords available]

Indexed keywords

1 (4' METHOXYBIPHENYL 4 YL) 5 METHYLOCTAHYDROPYRROLO[3,4 B]PYRROLE; 1 [4' (5 METHYLHEXAHYDROPYRROLO[3,4 B]PYRROL 1 YL)BIPHENYL 4 YL]ETHANONE; 4' (5 METHYLHEXAHYDROPYRROLO[3,4 B]PYRROL 1 YL)BIPHENYL 4 CARBONITRILE; 5 (4 CYANOPHENYL) 2 [2 (2 METHYL 1 IMIDAZOLIDINYL)ETHYL]BENZOFURAN; 5 METHYLOCTAHYDROPYRROLO[3,4 B]PYRROLE; BENZO[4,5]HYDRINDENO[1,7 AC] 1 BENZYLPYRROLIDINE DERIVATIVE; BENZOFURAN DERIVATIVE; CONESSINE; G PROTEIN COUPLED RECEPTOR; HISTAMINE H3 RECEPTOR; HISTAMINE H3 RECEPTOR ANTAGONIST; PYRROLE DERIVATIVE; PYRROLIDINE DERIVATIVE; PYRROLO[3,4 B]PYRROLE DERIVATIVE; TRITIUM; UNCLASSIFIED DRUG;

EID: 68549132508     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm900480x     Document Type: Article
Times cited : (10)

References (30)
  • 5
    • 0035146803 scopus 로고    scopus 로고
    • The physiology of brain histamine
    • (c) Brown, R. E.; Stevens, D. R.; Haas, H. L. The physiology of brain histamine. Prog. Neurobiol. 2001, 63 (6), 637-672.
    • (2001) Prog. Neurobiol , vol.63 , Issue.6 , pp. 637-672
    • Brown, R.E.1    Stevens, D.R.2    Haas, H.L.3
  • 8
    • 33645287272 scopus 로고    scopus 로고
    • 3 receptor antagonists: Preclinical promise for treating obesity and cognitive disorders
    • 3 receptor antagonists: preclinical promise for treating obesity and cognitive disorders. Mol. Interventions 2006, 6 (2), 77-88.
    • (2006) Mol. Interventions , vol.6 , Issue.2 , pp. 77-88
    • Esbenshade, T.A.1    Fox, G.B.2    Cowart, M.D.3
  • 10
    • 34248562939 scopus 로고    scopus 로고
    • 3 receptors in Alzheimer's disease brain and improves cognitive performance in preclinical models. J. Pharmacol. Exp. Ther. 2007, 321 (3), 1032-1045.
    • 3 receptors in Alzheimer's disease brain and improves cognitive performance in preclinical models. J. Pharmacol. Exp. Ther. 2007, 321 (3), 1032-1045.
  • 11
    • 0027179068 scopus 로고
    • Involvement of histamine in the control of the waking state
    • Monti, J. M. Involvement of histamine in the control of the waking state. Life Sci. 1993, 53, 1331-1338.
    • (1993) Life Sci , vol.53 , pp. 1331-1338
    • Monti, J.M.1
  • 12
    • 0023072654 scopus 로고
    • Attention deficit disorder with hyperactivity (ADDH): The contribution of catecholaminergic activity
    • Oades, R. D. Attention deficit disorder with hyperactivity (ADDH): The contribution of catecholaminergic activity. Prog. Neurobiol. 1987, 29 (4), 365-391.
    • (1987) Prog. Neurobiol , vol.29 , Issue.4 , pp. 365-391
    • Oades, R.D.1
  • 13
    • 0033390894 scopus 로고    scopus 로고
    • Cognitive dysfunction in schizophrenia and its importance to outcome: The place of atypical antipsychotics in treatment
    • Velligan, D. I.; Miller, A. L. Cognitive dysfunction in schizophrenia and its importance to outcome: the place of atypical antipsychotics in treatment. J. Clin. Psychiatry 1999, 60, 25-28.
    • (1999) J. Clin. Psychiatry , vol.60 , pp. 25-28
    • Velligan, D.I.1    Miller, A.L.2
  • 14
    • 51849125301 scopus 로고
    • (a) Ulrici, F. Conessine. Arch Pharm. 1918, 256, 57-80.
    • (1918) Arch Pharm , vol.256 , pp. 57-80
    • Ulrici, F.C.1
  • 16
    • 51849134749 scopus 로고
    • 18-oxygenated steroids: The constitution of conessine
    • (c) McNiven, N. L. Some simple 18-oxygenated steroids: the constitution of conessine. Chem. Ind. 1957, 1296-1297.
    • (1957) Chem. Ind , pp. 1296-1297
    • McNiven, N.1    Some simple, L.2
  • 18
    • 0029999489 scopus 로고    scopus 로고
    • An Asymmetric Route to the Conanine BCDE Ring System. A Formal Total Synthesis of (+)-Conessine
    • Kopach, M. E.; Fray, A. H.; Meyers, A. I. An Asymmetric Route to the Conanine BCDE Ring System. A Formal Total Synthesis of (+)-Conessine. J. Am. Chem. Soc. 1996, 118, 9876-9883.
    • (1996) J. Am. Chem. Soc , vol.118 , pp. 9876-9883
    • Kopach, M.E.1    Fray, A.H.2    Meyers, A.I.3
  • 21
    • 9344236011 scopus 로고    scopus 로고
    • Li, Q.; Chu, D. T. W.; Claiborne, A.; Cooper, C. S.; Lee, C. M.; Raye, K.; Berst, K. B.; Donner, P.; Wang, W.; Hasvold, L.; Fung, A.; Ma, Z.; Tufano, M.; Flamm, R.; Shen, L. L.; Baranowski, J.; Nilius, A.; Alder, J.; Meulbroek, J.; Marsh, K.; Crowell, D.; Hui, Y.; Seif, L.; Melcher, L. M.; Henry, R.; Spanton, S.; Faghih, R.; Klein, L. L.; Tanaka, S. K.; Plattner, J. J. Synthesis and Structure-Activity Relationships of 2-Pyridones: A Novel Series of Potent DNA Gyrase Inhibitors as Antibacterial Agents. J. Med. Chem. 1996, 39 (16), 3070-3088.
    • (a) Li, Q.; Chu, D. T. W.; Claiborne, A.; Cooper, C. S.; Lee, C. M.; Raye, K.; Berst, K. B.; Donner, P.; Wang, W.; Hasvold, L.; Fung, A.; Ma, Z.; Tufano, M.; Flamm, R.; Shen, L. L.; Baranowski, J.; Nilius, A.; Alder, J.; Meulbroek, J.; Marsh, K.; Crowell, D.; Hui, Y.; Seif, L.; Melcher, L. M.; Henry, R.; Spanton, S.; Faghih, R.; Klein, L. L.; Tanaka, S. K.; Plattner, J. J. Synthesis and Structure-Activity Relationships of 2-Pyridones: A Novel Series of Potent DNA Gyrase Inhibitors as Antibacterial Agents. J. Med. Chem. 1996, 39 (16), 3070-3088.
  • 22
    • 68549101185 scopus 로고    scopus 로고
    • 3aR,6aR-Hexahydro-pyrrolo[3,4-b] pyrrole-1-carboxylic acid tert-butyl ester (18, CAS no. 370880-09-4) may be prepared as described in Basha, A, Bunnelle, W. H, Dart, M. J.;Gallagher, M. E, Ji, J, Li, T, Pace, J. M, Ryther, K. B, Tietje, K. R, Mortell, K. H, Nersesian, D. L, Schrimpf, M. R. Substituted diazabicycloalkane derivatives. U.S. Pat. Appl. Publ. 2005101602A1, 2005
    • (b) (3aR,6aR)-Hexahydro-pyrrolo[3,4-b] pyrrole-1-carboxylic acid tert-butyl ester (18, CAS no. 370880-09-4) may be prepared as described in Basha, A.; Bunnelle, W. H.; Dart, M. J.;Gallagher, M. E.; Ji, J.; Li, T.; Pace, J. M.; Ryther, K. B.; Tietje, K. R.; Mortell, K. H.; Nersesian, D. L.; Schrimpf, M. R. Substituted diazabicycloalkane derivatives. U.S. Pat. Appl. Publ. 2005101602A1, 2005.
  • 23
    • 68549116671 scopus 로고    scopus 로고
    • 3 receptor for the treatment of neurological disorders. PCT Int. Appl. WO2004056369A1, 2004.
    • 3 receptor for the treatment of neurological disorders. PCT Int. Appl. WO2004056369A1, 2004.
  • 25
    • 29144437722 scopus 로고    scopus 로고
    • Keynote review: Histamine H3 receptor antagonists reach out for the clinic
    • Celanire, S.; Wijtmans, M.; Talaga, P.; Leurs, R.; de Esch, I. J. P. Keynote review: Histamine H3 receptor antagonists reach out for the clinic. Drug Discovery Today 2005, 10 (23/24), 1613-1627.
    • (2005) Drug Discovery Today , vol.10 , Issue.23-24 , pp. 1613-1627
    • Celanire, S.1    Wijtmans, M.2    Talaga, P.3    Leurs, R.4    de Esch, I.J.P.5
  • 26
    • 68549120184 scopus 로고    scopus 로고
    • Schwink, L.; Stengelin, S.; Gossel, M.; Hessler, G.; Lennig, P. Preparation of 2,7-diazabicyclo[3.3.0]octanes and related compounds as antiobesity agents. PCT Int. Appl. WO2006018280A2, 2006.
    • (a) Schwink, L.; Stengelin, S.; Gossel, M.; Hessler, G.; Lennig, P. Preparation of 2,7-diazabicyclo[3.3.0]octanes and related compounds as antiobesity agents. PCT Int. Appl. WO2006018280A2, 2006.
  • 27
    • 68549130151 scopus 로고    scopus 로고
    • Preparation of substituted bicyclic 8-pyrrolidino-xanthines and use thereof as inhibitors of the dipeptidyl peptidase IV
    • PCT Int. Appl. WO 2006015699 A1
    • (b) Schoenafinger, K.; Jaehne, G.; Defossa, E.; Schwink, L.; Wagner, H.; Buning, C.; Tschank, G.; Werner, U. Preparation of substituted bicyclic 8-pyrrolidino-xanthines and use thereof as inhibitors of the dipeptidyl peptidase IV. PCT Int. Appl. WO 2006015699 A1, 2006.
    • (2006)
    • Schoenafinger, K.1    Jaehne, G.2    Defossa, E.3    Schwink, L.4    Wagner, H.5    Buning, C.6    Tschank, G.7    Werner, U.8
  • 29
    • 35848962986 scopus 로고    scopus 로고
    • Ji, J.; Schrimpf, M. R.; Sippy, K. B.; Bunnelle, W. H.; Li, T.; Anderson, D. J.; Faltynek, C.; Surowy, C. S.; Dyhring, T.; Ahring, P. K.; Meyer, M. D. Synthesis and Structure - Activity Relationship Studies of 3,6-Diazabicyclo[3.2.0]heptanes as Novel α4β2 Nicotinic Acetylcholine Receptor Selective Agonists. J. Med. Chem. 2007, 50 (22), 5493-5508.
    • (a) Ji, J.; Schrimpf, M. R.; Sippy, K. B.; Bunnelle, W. H.; Li, T.; Anderson, D. J.; Faltynek, C.; Surowy, C. S.; Dyhring, T.; Ahring, P. K.; Meyer, M. D. Synthesis and Structure - Activity Relationship Studies of 3,6-Diazabicyclo[3.2.0]heptanes as Novel α4β2 Nicotinic Acetylcholine Receptor Selective Agonists. J. Med. Chem. 2007, 50 (22), 5493-5508.
  • 30
    • 85054488442 scopus 로고    scopus 로고
    • Preparation of amino-substituted tricyclic derivatives as modulators of alpha7 nicotinic receptors and methods of use
    • U.S. Pat. Appl. Publ. 2005234031A1, 2005
    • (b) Schrimpf, M. R.; Sippy, K. B.; Ji, J.; Li, T.; Frost, J. M.; Briggs, C. A.; Bunnelle, W. H. Preparation of amino-substituted tricyclic derivatives as modulators of alpha7 nicotinic receptors and methods of use. U.S. Pat. Appl. Publ. 2005234031A1, 2005.
    • Schrimpf, M.R.1    Sippy, K.B.2    Ji, J.3    Li, T.4    Frost, J.M.5    Briggs, C.A.6    Bunnelle, W.H.7


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.