메뉴 건너뛰기




Volumn 53, Issue 19, 2010, Pages 7219-7228

Bioisosteric replacement leading to biologically active [2.2]Paracyclophanes with altered binding profiles for aminergic g-protein-coupled receptors

Author keywords

[No Author keywords available]

Indexed keywords

1 (2,5 DIMETHYLPHENYL) 4 [4 (2,5 DIMETHYLPHENYL) 4 HYDROXYPIPERIDIN 1 YL]BUTAN 1 ONE; 1 (2,5 DIMETHYLPHENYL) 4 [4 (2,5 DIMETHYLPHENYL)PIPERAZIN 1 YL]BUTAN 1 ONE; 1 (4 FUOROPHENYL) 4 [4 [[2.2]PARACYCLOPHAN 4 YL] 4 HYDROXYPIPERIDIN 1 YL]BUTAN 1 ONE; 1 [2,5 DIMETHYLPHENYL)] 4 [1,4 DIOXA 8 AZASPIRO[4.5]DEC 8 YL]BUTAN 1 ONE; 1 [2,5 DIMETHYLPHENYL] 4 [1,4 DIOXA 8 AZASPIRO[4.5]DEC 8 YL]BUTAN 1 ONE; 1 [4 (2,5 DIMETHYLPHENYL) 4 OXOBUTYL]PIPERIDIN 4 ONE; 1 [4 (4 FLUOROPHENYL) 4 OXOBUTYL]PIPERIDIN 4 ONE; 1 [4 [[2.2]PARACYCLOPHAN 4 YL] 4 OXOBUTYL]PIPERIDIN 4 ONE; 1 [[2.2]PARACYCLOPHAN 4 YL] 4 [1,4 DIOXA 8 AZASPIRO[4.5]DEC 8 YL]BUTAN 1 ONE; 4 BROMO 1 (2,5 DIMETHYLPHENYL)BUTAN 1 ONE; 4 BROMO 1 [[2.2]PARACYCLOPHAN 4 YL]BUTAN 1 ONE; 4 [1,4 DIOXA 8 AZASPIRO[4.5]DEC 8 YL] 1 (4 FLUOROPHENYL)BUTAN 1 ONE; 4 [4 (2 METHOXYPHENYL)PIPERAZIN 1 YL]BUTYRONITRILE; 4 [4 (2,5 DIMETHYLPHENYL) 4 HYDROXYPIPERIDIN 1 YL] 1 (4 FLUOROPHENYL)BUTAN 1 ONE; 4 [4 (2,5 DIMETHYLPHENYL)PIPERAZIN 1 YL] 1 (4 FLUOROPHENYL)BUTAN 1 ONE; 4 [4 (4 CHLOROPHENYL) 4 HYDROXYPIPERIDIN 1 YL] 1 (2,5 DIMETHYLPHENYL)BUTAN 1 ONE; 4 [4 (4 CHLOROPHENYL) 4 HYDROXYPIPERIDIN 1 YL] 1 [[2.2]PARACYCLOPHAN 4 YL]BUTAN 1 ONE; 4 [4 (4 CHLOROPHENYL)PIPERAZIN 1 YL] 1 (2,5 DIMETHYLPHENYL)BUTAN 1 ONE; 4 [4 (4 CHLOROPHENYL)PIPERAZIN 1 YL] 1 (4 FLUOROPHENYL)BUTAN 1 ONE; 4 [4 (4 CHLOROPHENYL)PIPERAZIN 1 YL] 1 [[2.2]PARACYCLOPHAN 4 YL]BUTAN 1 ONE; 4 [4 [[2.2]PARACYCLOPHAN 4 YL] 4 HYDROXYPIPERIDIN 1 YL] 1 [[2.2]PARACYCLOPHAN 4 YL]BUTAN 1 ONE; 4 [4 [[2.2]PARACYCLOPHAN 4 YL]PIPERAZIN 1 YL] 1 (4 FLUOROPHENYL)BUTAN 1 ONE; 4 [4 [[2.2]PARACYCLOPHAN 4 YL]PIPERAZIN 1 YL] 1 [[2.2]PARACYCLOPHAN 4 YL]BUTAN 1 ONE; 4 [4 [[2.2]PARACYCLOPHAN 4 YL]PIPERAZIN 1 YL]BUTYRONITRILE; G PROTEIN COUPLED RECEPTOR; PARACYCLOPHANE DERIVATIVE; PIPERAZINE DERIVATIVE; SEROTONIN 1 RECEPTOR; SEROTONIN 1A RECEPTOR; UNCLASSIFIED DRUG; UNINDEXED DRUG; ALPHA 1 ADRENERGIC RECEPTOR; DOPAMINE RECEPTOR; LIGAND; N-(4-(4-((2.2)PARACYCLOPHAN-4-YL)PIPERAZIN-1-YL)BUTYL)BENZO(B)THIOPHENYL-2-CARBOXAMIDE; SEROTONIN RECEPTOR; THIOPHENE DERIVATIVE;

EID: 77957920179     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm100899z     Document Type: Article
Times cited : (13)

References (31)
  • 1
    • 62649174043 scopus 로고    scopus 로고
    • The consolidation of neuroleptic therapy: Janssen, the discovery of haloperidol and its introduction into clinical practice
    • Lopez-Munoz, F.; Alamo, C. The consolidation of neuroleptic therapy: Janssen, the discovery of haloperidol and its introduction into clinical practice Brain Res. Bull. 2009, 79, 130-141
    • (2009) Brain Res. Bull. , vol.79 , pp. 130-141
    • Lopez-Munoz, F.1    Alamo, C.2
  • 2
    • 70349117637 scopus 로고    scopus 로고
    • Iloperidone: In schizophrenia
    • Scott, L. J. Iloperidone: in schizophrenia CNS Drugs 2009, 23, 867-880
    • (2009) CNS Drugs , vol.23 , pp. 867-880
    • Scott, L.J.1
  • 3
    • 72449129531 scopus 로고    scopus 로고
    • Paliperidone palmitate - Review of the efficacy, safety and cost of a new second-generation depot antipsychotic medication
    • Citrome, L. Paliperidone palmitate - review of the efficacy, safety and cost of a new second-generation depot antipsychotic medication Int. J. Clin. Pract. 2010, 64, 216-239
    • (2010) Int. J. Clin. Pract. , vol.64 , pp. 216-239
    • Citrome, L.1
  • 5
    • 4344714861 scopus 로고    scopus 로고
    • Aripiprazole. A review of its use in schizophrenia and schizoaffective disorder
    • Harrison, T. S.; Perry, C. M. Aripiprazole. A review of its use in schizophrenia and schizoaffective disorder Drugs 2004, 64, 1715-1736
    • (2004) Drugs , vol.64 , pp. 1715-1736
    • Harrison, T.S.1    Perry, C.M.2
  • 6
    • 0025300269 scopus 로고
    • The discovery and development of buspirone: A new approach to the treatment of anxiety
    • New, J. S. The discovery and development of buspirone: a new approach to the treatment of anxiety Med. Res. Rev. 1990, 10, 283-326
    • (1990) Med. Res. Rev. , vol.10 , pp. 283-326
    • New, J.S.1
  • 7
    • 34250884564 scopus 로고    scopus 로고
    • Curative-like analgesia in a neuropathic pain model: Parametric analysis of the dose and the duration of treatment with a high-efficacy 5-HT1A receptor agonist
    • Deseure, K.; Breand, S.; Colpaert, F. C. Curative-like analgesia in a neuropathic pain model: Parametric analysis of the dose and the duration of treatment with a high-efficacy 5-HT1A receptor agonist Eur. J. Pharmacol. 2007, 568, 134-141
    • (2007) Eur. J. Pharmacol. , vol.568 , pp. 134-141
    • Deseure, K.1    Breand, S.2    Colpaert, F.C.3
  • 10
    • 0037057547 scopus 로고    scopus 로고
    • Interactive SAR studies: Rational discovery of super-potent and highly selective dopamine D3 receptor antagonists and partial agonists
    • Bettinetti, L.; Schlotter, K.; Hübner, H.; Gmeiner, P. Interactive SAR studies: rational discovery of super-potent and highly selective dopamine D3 receptor antagonists and partial agonists J. Med. Chem. 2002, 45, 4594-4597
    • (2002) J. Med. Chem. , vol.45 , pp. 4594-4597
    • Bettinetti, L.1    Schlotter, K.2    Hübner, H.3    Gmeiner, P.4
  • 11
    • 9444228286 scopus 로고    scopus 로고
    • Certain 1,4-disubstituted aromatic piperidines and piperazines with extreme selectivity for the dopamine D4 receptor interact with a common receptor microdomain
    • Kortagere, S.; Gmeiner, P.; Weinstein, H.; Schetz, J. A. Certain 1,4-disubstituted aromatic piperidines and piperazines with extreme selectivity for the dopamine D4 receptor interact with a common receptor microdomain Mol. Pharmacol. 2004, 66, 1491-1499
    • (2004) Mol. Pharmacol. , vol.66 , pp. 1491-1499
    • Kortagere, S.1    Gmeiner, P.2    Weinstein, H.3    Schetz, J.A.4
  • 12
    • 68549110381 scopus 로고    scopus 로고
    • Dopamine D2, D3, and D4 selective phenylpiperazines as molecular probes to explore the origins of subtype specific receptor binding
    • Ehrlich, K.; Götz, A.; Bollinger, S.; Tschammer, N.; Bettinetti, L.; Härterich, S.; Hübner, H.; Lanig, H.; Gmeiner, P. Dopamine D2, D3, and D4 selective phenylpiperazines as molecular probes to explore the origins of subtype specific receptor binding J. Med. Chem. 2009, 52, 4923-4935
    • (2009) J. Med. Chem. , vol.52 , pp. 4923-4935
    • Ehrlich, K.1    Götz, A.2    Bollinger, S.3    Tschammer, N.4    Bettinetti, L.5    Härterich, S.6    Hübner, H.7    Lanig, H.8    Gmeiner, P.9
  • 13
    • 33745182275 scopus 로고    scopus 로고
    • Fancy bioisosteres: Novel paracyclophane derivatives as super-affinity dopamine D3 receptor antagonists
    • Schlotter, K.; Böckler, F.; Hübner, H.; Gmeiner, P. Fancy bioisosteres: novel paracyclophane derivatives as super-affinity dopamine D3 receptor antagonists J. Med. Chem. 2006, 49, 3628-3635
    • (2006) J. Med. Chem. , vol.49 , pp. 3628-3635
    • Schlotter, K.1    Böckler, F.2    Hübner, H.3    Gmeiner, P.4
  • 14
    • 0035794960 scopus 로고    scopus 로고
    • Indoloparacyclophanes: Synthesis and dopamine receptor binding of a novel arylbioisostere
    • Ortner, B.; Waibel, R.; Gmeiner, P. Indoloparacyclophanes: synthesis and dopamine receptor binding of a novel arylbioisostere Angew. Chem, Int. Ed. 2001, 40, 1283-1285
    • (2001) Angew. Chem, Int. Ed. , vol.40 , pp. 1283-1285
    • Ortner, B.1    Waibel, R.2    Gmeiner, P.3
  • 15
    • 0037206785 scopus 로고    scopus 로고
    • Analogs of the dopamine D4 receptor ligand FAUC 113 with planar- and central-chirality
    • Löber, S.; Ortner, B.; Bettinetti, L.; Hübner, H.; Gmeiner, P. Analogs of the dopamine D4 receptor ligand FAUC 113 with planar- and central-chirality Tetrahedron: Asymmetry 2002, 13, 2303
    • (2002) Tetrahedron: Asymmetry , vol.13 , pp. 2303
    • Löber, S.1    Ortner, B.2    Bettinetti, L.3    Hübner, H.4    Gmeiner, P.5
  • 16
    • 0038248584 scopus 로고    scopus 로고
    • Conjugated enynes as nonaromatic catechol bioisosteres: Synthesis, binding experiments, and computational studies of novel dopamine receptor agonists recognizing preferentially the D3 subtype
    • Hübner, H.; Haubmann, C.; Utz, W.; Gmeiner, P. Conjugated enynes as nonaromatic catechol bioisosteres: synthesis, binding experiments, and computational studies of novel dopamine receptor agonists recognizing preferentially the D3 subtype J. Med. Chem. 2000, 43, 756-762
    • (2000) J. Med. Chem. , vol.43 , pp. 756-762
    • Hübner, H.1    Haubmann, C.2    Utz, W.3    Gmeiner, P.4
  • 17
    • 0026695537 scopus 로고
    • Structural subtypes of the dopamine D2 receptor are functionally distinct: Expression of the cloned D2A and D2B subtypes in a heterologous cell line
    • Hayes, G.; Biden, T. J.; Selbie, L. A.; Shine, J. Structural subtypes of the dopamine D2 receptor are functionally distinct: expression of the cloned D2A and D2B subtypes in a heterologous cell line Mol. Endocrinol. 1992, 6, 920-926
    • (1992) Mol. Endocrinol. , vol.6 , pp. 920-926
    • Hayes, G.1    Biden, T.J.2    Selbie, L.A.3    Shine, J.4
  • 19
    • 0029120447 scopus 로고
    • Modulation of intracellular cyclic AMP levels by different human dopamine D4 receptor variants
    • Asghari, V.; Sanyal, S.; Buchwaldt, S.; Paterson, A.; Jovanovic, V.; Van Tol, H. H. M. Modulation of intracellular cyclic AMP levels by different human dopamine D4 receptor variants J. Neurochem. 1995, 65, 1157-1165
    • (1995) J. Neurochem. , vol.65 , pp. 1157-1165
    • Asghari, V.1    Sanyal, S.2    Buchwaldt, S.3    Paterson, A.4    Jovanovic, V.5    Van Tol, H.H.M.6
  • 20
    • 21044451732 scopus 로고    scopus 로고
    • GPCR antitarget modeling: Pharmacophore models for biogenic amine binding GPCRs to avoid GPCR-mediated side effects
    • Klabunde, T.; Evers, A. GPCR antitarget modeling: pharmacophore models for biogenic amine binding GPCRs to avoid GPCR-mediated side effects ChemBioChem 2005, 6, 876-889
    • (2005) ChemBioChem , vol.6 , pp. 876-889
    • Klabunde, T.1    Evers, A.2
  • 22
    • 0034676321 scopus 로고    scopus 로고
    • Cyanoindole derivatives as highly selective dopamine D4 receptor partial agonists: Solid-phase synthesis, binding assays, and functional experiments
    • Hübner, H.; Kraxner, J.; Gmeiner, P. Cyanoindole derivatives as highly selective dopamine D4 receptor partial agonists: solid-phase synthesis, binding assays, and functional experiments J. Med. Chem. 2000, 43, 4563-4569
    • (2000) J. Med. Chem. , vol.43 , pp. 4563-4569
    • Hübner, H.1    Kraxner, J.2    Gmeiner, P.3
  • 23
    • 17144424958 scopus 로고    scopus 로고
    • CoMFA and CoMSIA investigations revealing novel insights into the binding modes of dopamine D3 receptor agonists
    • Boeckler, F.; Ohnmacht, U.; Lehmann, T.; Utz, W.; Hübner, H.; Gmeiner, P. CoMFA and CoMSIA investigations revealing novel insights into the binding modes of dopamine D3 receptor agonists J. Med. Chem. 2005, 48, 2493-2508
    • (2005) J. Med. Chem. , vol.48 , pp. 2493-2508
    • Boeckler, F.1    Ohnmacht, U.2    Lehmann, T.3    Utz, W.4    Hübner, H.5    Gmeiner, P.6
  • 24
    • 0028971630 scopus 로고
    • Hydrophobic residues of the D2 dopamine receptor are important for binding and signal transduction
    • Cho, W.; Taylor, L. P.; Mansour, A.; Akil, H. Hydrophobic residues of the D2 dopamine receptor are important for binding and signal transduction J. Neurochem. 1995, 65, 2105-2115
    • (1995) J. Neurochem. , vol.65 , pp. 2105-2115
    • Cho, W.1    Taylor, L.P.2    Mansour, A.3    Akil, H.4
  • 25
    • 0032570306 scopus 로고    scopus 로고
    • A cluster of aromatic residues in the sixth membrane-spanning segment of the dopamine D2 receptor is accessible in the binding-site crevice
    • Javitch, J. A.; Ballersteros, J. A.; Weinstein, H.; Chen, J. A cluster of aromatic residues in the sixth membrane-spanning segment of the dopamine D2 receptor is accessible in the binding-site crevice Biochemistry 1998, 37, 998-1006
    • (1998) Biochemistry , vol.37 , pp. 998-1006
    • Javitch, J.A.1    Ballersteros, J.A.2    Weinstein, H.3    Chen, J.4
  • 26
    • 77952121371 scopus 로고    scopus 로고
    • Engineering a GPCR-ligand pair that simulates the activation of D2L by dopamine
    • Tschammer, N.; Dörfler, M.; Hübner, H.; Gmeiner, P. Engineering a GPCR-ligand pair that simulates the activation of D2L by dopamine ACS Chem. Neurosci. 2010, 1, 25-35
    • (2010) ACS Chem. Neurosci. , vol.1 , pp. 25-35
    • Tschammer, N.1    Dörfler, M.2    Hübner, H.3    Gmeiner, P.4
  • 27
    • 85069282894 scopus 로고
    • U.S. Patent US 2997472
    • Janssen, P. A. J. U.S. Patent US 2997472, 1961.
    • (1961)
    • Janssen, P.A.J.1
  • 28
    • 20144375764 scopus 로고    scopus 로고
    • Fancy bioisosteres: Metallocene-derived G-protein-coupled receptor ligands with subnanomolar binding affinity and novel selectivity profiles
    • Schlotter, K.; Boeckler, F.; Hübner, H.; Gmeiner, P. Fancy bioisosteres: metallocene-derived G-protein-coupled receptor ligands with subnanomolar binding affinity and novel selectivity profiles J. Med. Chem. 2005, 48, 3696-3699
    • (2005) J. Med. Chem. , vol.48 , pp. 3696-3699
    • Schlotter, K.1    Boeckler, F.2    Hübner, H.3    Gmeiner, P.4
  • 30
    • 56249118049 scopus 로고    scopus 로고
    • Novel D3 selective dopaminergics incorporating enyne units as nonaromatic catechol bioisosteres: Synthesis, bioactivity, and mutagenesis studies
    • Dörfler, M.; Tschammer, N.; Hamperl, K.; Hübner, H.; Gmeiner, P. Novel D3 selective dopaminergics incorporating enyne units as nonaromatic catechol bioisosteres: synthesis, bioactivity, and mutagenesis studies J. Med. Chem. 2008, 51, 6829-6838
    • (2008) J. Med. Chem. , vol.51 , pp. 6829-6838
    • Dörfler, M.1    Tschammer, N.2    Hamperl, K.3    Hübner, H.4    Gmeiner, P.5


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.