메뉴 건너뛰기




Volumn 39, Issue 21, 1996, Pages 4238-4246

Synthesis, resolution, and preliminary evaluation of trans-2-amino- 6(5)-hydroxy-1-phenyl-2,3-dihydro-1H-indenes and related derivatives as dopamine receptors ligands

Author keywords

[No Author keywords available]

Indexed keywords

DOPAMINE 1 RECEPTOR STIMULATING AGENT; DOPAMINE 2 RECEPTOR STIMULATING AGENT; INDENE DERIVATIVE;

EID: 0029825971     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm960318v     Document Type: Article
Times cited : (12)

References (30)
  • 5
    • 0025298537 scopus 로고
    • Trans-10,11-Dihydroxy-5,6,6a,7,8,12b-hexahydro[a]-phenanthridine: A Highly Potent Selective Dopamine Full Agonist
    • Brewster, W. K.; Nichols, D. E.; Riggs, R. M.; Mottola, D. M.; Lovemberg, T. W;; Lewis, M. H.; Mailman, R. B. Trans-10,11-Dihydroxy-5,6,6a,7,8,12b-hexahydro[a]-phenanthridine: A Highly Potent Selective Dopamine Full Agonist. J. Med. Chem. 1990, 33, 1756-1764.
    • (1990) J. Med. Chem. , vol.33 , pp. 1756-1764
    • Brewster, W.K.1    Nichols, D.E.2    Riggs, R.M.3    Mottola, D.M.4    Lovemberg, T.W.5    Lewis, M.H.6    Mailman, R.B.7
  • 6
    • 0020370936 scopus 로고
    • Absolute Stereochemistry and Dopaminergic Activity of Enantiomers of 2,3,4,5-Tetrahydro-7,8-dihydroxy-1-pheny-1H-3-benzazepine
    • Kaiser, C.; Dandridge, P. A.; Garvey, E.; Hahn, R. A.; Sarau, H. M.; Setler, P.E.; Bass, L. S.; Clardy, J. Absolute Stereochemistry and Dopaminergic Activity of Enantiomers of 2,3,4,5-Tetrahydro-7,8-dihydroxy-1-pheny-1H-3-benzazepine. J. Med. Chem. 1982, 25, 697-703.
    • (1982) J. Med. Chem. , vol.25 , pp. 697-703
    • Kaiser, C.1    Dandridge, P.A.2    Garvey, E.3    Hahn, R.A.4    Sarau, H.M.5    Setler, P.E.6    Bass, L.S.7    Clardy, J.8
  • 7
    • 85023555208 scopus 로고
    • Preparation of Phenanthridine Compounds as Dopamine Agonists. PCT Int. Appl. WO 9204,356
    • Kebabian, J. W.; Michaelides, M. R.; Schoenleber, R. W. (Abbott Laboratories). Preparation of Phenanthridine Compounds as Dopamine Agonists. PCT Int. Appl. WO 9204,356; Annu. Drug Data Rep. 1992, 14, 765.
    • (1992) Annu. Drug Data Rep. , vol.14 , pp. 765
    • Kebabian, J.W.1    Michaelides, M.R.2    Schoenleber, R.W.3
  • 10
    • 0022272987 scopus 로고
    • Dopamine Agonists: Structure-activity Relationships
    • Jucker, E., Ed.; Birkhauser: Basel
    • (a) Cannon, J. G. Dopamine Agonists: Structure-activity Relationships. In Progress in Drug Research; Jucker, E., Ed.; Birkhauser: Basel, 1985; Vol. 29, pp 303-414.
    • (1985) Progress in Drug Research , vol.29 , pp. 303-414
    • Cannon, J.G.1
  • 12
    • 10244226525 scopus 로고
    • Condensation and Addition Reactions of 3-Phenylindene
    • Weinstein, B. Condensation and Addition Reactions of 3-Phenylindene. J. Org. Chem. 1961, 26, 4161-4162.
    • (1961) J. Org. Chem. , vol.26 , pp. 4161-4162
    • Weinstein, B.1
  • 13
    • 0141833866 scopus 로고
    • A Stereospecific Synthesis of Alicyclic and Bicyclic Amines via Hydroboration
    • Rathke, M. W.; Inoue, N.; Varma, K. R.; Brown, H. C. A Stereospecific Synthesis of Alicyclic and Bicyclic Amines via Hydroboration. J. Am. Chem. Soc. 1966, 88, 2870-2871.
    • (1966) J. Am. Chem. Soc. , vol.88 , pp. 2870-2871
    • Rathke, M.W.1    Inoue, N.2    Varma, K.R.3    Brown, H.C.4
  • 14
    • 0008700461 scopus 로고
    • Benzo- and Indoloquinolizidine derivatives XIX. the Synthesis and Pharmacological Activity of Some Quinolizidine Derivatives, Analogues of Butaclamol
    • Laus, G.; Tourwé, D.; Van Bist, G. Benzo- and Indoloquinolizidine derivatives XIX. The Synthesis and Pharmacological Activity of Some Quinolizidine Derivatives, Analogues of Butaclamol. Heterocycles 1984, 22, 311-331.
    • (1984) Heterocycles , vol.22 , pp. 311-331
    • Laus, G.1    Tourwé, D.2    Van Bist, G.3
  • 15
    • 0027296081 scopus 로고
    • 2,5-Dimethoxy Congeners of (+)- and (-)-3-(3-Hydroxyphenyl)-N-n-propylpiperidine
    • Cannon, J. G.; Kirschbaum, S. K.; Amoo, V. E. D.; Johnson, A. K.; Long, J. P. 2,5-Dimethoxy Congeners of (+)- and (-)-3-(3-Hydroxyphenyl)-N-n-propylpiperidine. J. Med. Chem. 1993, 36, 2416-2419.
    • (1993) J. Med. Chem. , vol.36 , pp. 2416-2419
    • Cannon, J.G.1    Kirschbaum, S.K.2    Amoo, V.E.D.3    Johnson, A.K.4    Long, J.P.5
  • 16
    • 0000473171 scopus 로고
    • Sodium Borohydride-Carboxylic Acid Systems. Useful Reagents for the Alkylation of Amines
    • Marchini, P.; Liso, G.; Reho, A.; Liberatore, F.; Micheletti Moracci, F. Sodium Borohydride-Carboxylic Acid Systems. Useful Reagents for the Alkylation of Amines. J. Org. Chem. 1975, 40, 3453-3456.
    • (1975) J. Org. Chem. , vol.40 , pp. 3453-3456
    • Marchini, P.1    Liso, G.2    Reho, A.3    Liberatore, F.4    Micheletti Moracci, F.5
  • 17
    • 37049108561 scopus 로고
    • Regioselective Cleavage of Aromatic Methyl Ethers by Methanesulphonic Acid in the Presence of Methionine
    • Fujii, N.; Irie, H.; Yajima, H. Regioselective Cleavage of Aromatic Methyl Ethers by Methanesulphonic Acid in the Presence of Methionine. J. Chem. Soc., Perkin Trans, 1 1977, 2288-2289.
    • (1977) J. Chem. Soc., Perkin Trans, 1 , pp. 2288-2289
    • Fujii, N.1    Irie, H.2    Yajima, H.3
  • 18
  • 19
    • 0027533244 scopus 로고
    • Recent Advances in the Molecular Biology of Dopamine Receptors
    • Gingrich, J. A.; Caron, M. G. Recent Advances in the Molecular Biology of Dopamine Receptors. Annu. Rev. Neurosci. 1993, 16, 299-321.
    • (1993) Annu. Rev. Neurosci. , vol.16 , pp. 299-321
    • Gingrich, J.A.1    Caron, M.G.2
  • 20
    • 0025326730 scopus 로고
    • Conformational Analysis and Structure-Activity Relationships of Selective Dopamine D-1 Receptor Agonists and Antagonists of the Benzazepine Series
    • Petterson, I.; Liljefors, T.; Bøgesø, K. Conformational Analysis and Structure-Activity Relationships of Selective Dopamine D-1 Receptor Agonists and Antagonists of the Benzazepine Series. J. Med. Chem. 1990, 33, 2197-2204.
    • (1990) J. Med. Chem. , vol.33 , pp. 2197-2204
    • Petterson, I.1    Liljefors, T.2    Bøgesø, K.3
  • 22
    • 0001672496 scopus 로고
    • Enantioselectivity in the Binding of (+) and (-)-2-Amino-6,7-dihydroxy-1,2,3,4-tetrahydronaphtalene and Related Agonists to Dopamine Receptors
    • Usdin, E., Kopin, I. J., Barchas, J., Eds.; Pergamon Press: New York
    • McDermed, J. D.; Freeman H. S.; Ferris, R. M. Enantioselectivity in the Binding of (+) and (-)-2-Amino-6,7-dihydroxy-1,2,3,4-tetrahydronaphtalene and Related Agonists to Dopamine Receptors. In Catecholamines: Basic and Clinical Frontiers; Usdin, E., Kopin, I. J., Barchas, J., Eds.; Pergamon Press: New York, 1979; Vol. 1, pp 568-570.
    • (1979) Catecholamines: Basic and Clinical Frontiers , vol.1 , pp. 568-570
    • McDermed, J.D.1    Freeman, H.S.2    Ferris, R.M.3
  • 23
    • 0000180858 scopus 로고
    • Kaiser, C., Kebabian, J. W., Eds; ACS Symposium Series 224; American Chemical Society: Washington, DC
    • Nichols, D. E. In Dopamine Receptors; Kaiser, C., Kebabian, J. W., Eds; ACS Symposium Series 224; American Chemical Society: Washington, DC, 1983; pp 201-218.
    • (1983) Dopamine Receptors , pp. 201-218
    • Nichols, D.E.1
  • 24
    • 0026470314 scopus 로고
    • Dopamine Receptor Agonists. I. Synthesis and Pharmacological Evaluation of 4-Aryl-substituted Analogues of 6,7-Dihydroxy-2-aminotetralin (6,7-ADTN) and Related Indane Compounds
    • Bertolini, G.; Vecchietti, V.; Mabilia, M.; Norcini, G.; Restelli, A.; Santangelo, P.; Villa, A. M.; Casagrande, C. Dopamine Receptor Agonists. I. Synthesis and Pharmacological Evaluation of 4-Aryl-substituted Analogues of 6,7-Dihydroxy-2-aminotetralin (6,7-ADTN) and Related Indane Compounds. Eur. J. Med. Chem. 1992, 27, 663-672.
    • (1992) Eur. J. Med. Chem. , vol.27 , pp. 663-672
    • Bertolini, G.1    Vecchietti, V.2    Mabilia, M.3    Norcini, G.4    Restelli, A.5    Santangelo, P.6    Villa, A.M.7    Casagrande, C.8
  • 25
    • 0021289099 scopus 로고
    • Dopaminergic Behaviour Stereospecifically Promoted by the D-1 Agonist R-SK&F 38393 and Selectively Blocked by the D-1 AntagonistsSCH 23390
    • Molloy, A. G.; Waddington, J. L. Dopaminergic Behaviour Stereospecifically Promoted by the D-1 Agonist R-SK&F 38393 and Selectively Blocked by the D-1 AntagonistsSCH 23390. Psychopharmacology 1984, 82, 409-410.
    • (1984) Psychopharmacology , vol.82 , pp. 409-410
    • Molloy, A.G.1    Waddington, J.L.2
  • 26
    • 0022500309 scopus 로고
    • 2 Agonists and Antagonists on Velocity of Movement, Rearing and Grooming in the Mouse
    • 2 Agonists and Antagonists on Velocity of Movement, Rearing and Grooming in the Mouse. Neuropharmacology 1986, 25, 455-463.
    • (1986) Neuropharmacology , vol.25 , pp. 455-463
    • Starr, B.S.1    Starr, M.S.2
  • 28
    • 0029123857 scopus 로고
    • Behavioural Pharmacology of 'D-1-like' Dopamine Receptors: Further Subtyping, New Pharmacological Probes and Interactions with 'D-2-like' Receptors
    • Waddington, J. L.; Daly, S. A.; Downes, R. P.; Deveney, A. M.; McCauley, P. G.; O'Boyle, K. M. Behavioural Pharmacology of 'D-1-like' Dopamine Receptors: further Subtyping, New Pharmacological Probes and Interactions with 'D-2-like' Receptors Prog. Neuro-Psychopharmacol. Biol. Psychiat. 1995, 19, 811-831.
    • (1995) Prog. Neuro-Psychopharmacol. Biol. Psychiat. , vol.19 , pp. 811-831
    • Waddington, J.L.1    Daly, S.A.2    Downes, R.P.3    Deveney, A.M.4    McCauley, P.G.5    O'Boyle, K.M.6
  • 29
    • 0025057573 scopus 로고
    • New Putative Selective Agonists at the D-1 Dopamine Receptor: Behavioural and Neurochemical Comparison of CY 208-243 with SK&F 101384 and SK&F 103243
    • Murray, A. M.; Waddington, J. L. New Putative Selective Agonists at the D-1 Dopamine Receptor: Behavioural and Neurochemical Comparison of CY 208-243 with SK&F 101384 and SK&F 103243. Pharmacol. Biochem. Behav. 1990, 35, 105-110.
    • (1990) Pharmacol. Biochem. Behav. , vol.35 , pp. 105-110
    • Murray, A.M.1    Waddington, J.L.2
  • 30
    • 0016827472 scopus 로고
    • Induction of Excessive Grooming in the Rat by Intraventricular Application of Peptides Derived from ACTH. Structure-Activity Studies
    • Gispen, W. H.; Wiegant, V. M.; Greven, H. M.; De Wied, D. Induction of Excessive Grooming in the Rat by Intraventricular Application of Peptides Derived from ACTH. Structure-Activity Studies. Life Sc. 1975, 17, 645-652.
    • (1975) Life Sc. , vol.17 , pp. 645-652
    • Gispen, W.H.1    Wiegant, V.M.2    Greven, H.M.3    De Wied, D.4


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.