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Volumn 43, Issue 15, 2000, Pages 2871-2882

Synthesis and pharmacological evaluation of thiopyran analogues of the dopamine D3 receptor-selective agonist (4aR,10bR)-(+)-trans-3,4,4a,10b- tetrahydro-4-n-propyl-2H,5H-[1]benzopyrano[4,3-b]-1,4-oxazin-9-ol (PD 128907)

Author keywords

[No Author keywords available]

Indexed keywords

3,4,4A,10B TETRAHYDRO 4 PROPYL 2H,5H [1]BENZOPYRANO[4,3 B][1,4]OXAZIN 9 OL; BENZOPYRAN DERIVATIVE; DOPAMINE; DOPAMINE 2 RECEPTOR; DOPAMINE 3 RECEPTOR; DOPAMINE 3 RECEPTOR STIMULATING AGENT; SEROTONIN 1A RECEPTOR; THIOPYRAN DERIVATIVE;

EID: 0034721133     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm0000113     Document Type: Article
Times cited : (149)

References (56)
  • 1
    • 0027477681 scopus 로고
    • Structures of dopamine receptors
    • O'Dowd, B. F. Structures of dopamine receptors. J. Neurochem. 1993, 60, 804-816.
    • (1993) J. Neurochem. , vol.60 , pp. 804-816
    • O'Dowd, B.F.1
  • 2
    • 0029249615 scopus 로고
    • Molecular and chemical neuropharmacology of dopamine receptor subtypes
    • Ogawa, N. Molecular and chemical neuropharmacology of dopamine receptor subtypes. Acta Med. Okayama 1995, 49, 1-11.
    • (1995) Acta Med. Okayama , vol.49 , pp. 1-11
    • Ogawa, N.1
  • 3
    • 0025179967 scopus 로고
    • Molecular cloning and characterization of a novel dopamine receptor (D3) as a target for neuroleptics
    • Sokoloff, P.; Giros, B.; Martres, M. P.; Bouthenet, M. L.; Schwartz, J. C. Molecular cloning and characterization of a novel dopamine receptor (D3) as a target for neuroleptics. Nature 1990, 347, 146-151.
    • (1990) Nature , vol.347 , pp. 146-151
    • Sokoloff, P.1    Giros, B.2    Martres, M.P.3    Bouthenet, M.L.4    Schwartz, J.C.5
  • 6
    • 0026427253 scopus 로고
    • Cloning of the gene for a human dopamine D4 receptor with high affinity for the antipsychotic clozapine
    • Van Tol, H. H.; Bunzow, J. R.; Guan, H. C.; Sunahara, R. K.; Seeman, P.; Niznik, H. B.; Civelli, O. Cloning of the gene for a human dopamine D4 receptor with high affinity for the antipsychotic clozapine. Nature 1991, 350, 610-614.
    • (1991) Nature , vol.350 , pp. 610-614
    • Van Tol, H.H.1    Bunzow, J.R.2    Guan, H.C.3    Sunahara, R.K.4    Seeman, P.5    Niznik, H.B.6    Civelli, O.7
  • 7
    • 0030610305 scopus 로고    scopus 로고
    • The D3 dopamine receptor: Neurobiology and potential clinical relevance
    • Levant, B. The D3 dopamine receptor: neurobiology and potential clinical relevance. Pharmacol. Rev. 1997, 49, 231-252.
    • (1997) Pharmacol. Rev. , vol.49 , pp. 231-252
    • Levant, B.1
  • 8
    • 0032798705 scopus 로고    scopus 로고
    • Dopamine D3 receptors: From anatomy to neuropsychiatry
    • Joyce, J. N.; Gurevich, E. V. Dopamine D3 receptors: from anatomy to neuropsychiatry. Neurosci. News 1999, 2, 11-21.
    • (1999) Neurosci. News , vol.2 , pp. 11-21
    • Joyce, J.N.1    Gurevich, E.V.2
  • 9
    • 0028179597 scopus 로고
    • Locomotor inhibition by the D3 ligand R-(+)-7-OH-DPAT is independent of changes in dopamine release
    • Svensson, K.; Carlsson, A.; Waters, N. Locomotor inhibition by the D3 ligand R-(+)-7-OH-DPAT is independent of changes in dopamine release. J. Neural Transm. Gen. Sect. 1994, 95, 71-74.
    • (1994) J. Neural Transm. Gen. Sect. , vol.95 , pp. 71-74
    • Svensson, K.1    Carlsson, A.2    Waters, N.3
  • 11
    • 0027421346 scopus 로고
    • Evidence that striatal synthesis-inhibiting autoreceptors are dopamine D3 receptors
    • Meller, E.; Bohmaker, K.; Goldstein, M.; Basham, D. A. Evidence that striatal synthesis-inhibiting autoreceptors are dopamine D3 receptors. Eur. J. Pharmacol. 1993, 249, R5-R6.
    • (1993) Eur. J. Pharmacol. , vol.249
    • Meller, E.1    Bohmaker, K.2    Goldstein, M.3    Basham, D.A.4
  • 12
    • 0027194404 scopus 로고
    • Modulation of cocaine self-administration in the rat through D-3 dopamine receptors
    • Caine, S. B.; Koob, G. F. Modulation of cocaine self-administration in the rat through D-3 dopamine receptors. Science 1993, 260, 1814-1816.
    • (1993) Science , vol.260 , pp. 1814-1816
    • Caine, S.B.1    Koob, G.F.2
  • 14
    • 0029562808 scopus 로고
    • Functional correlates of dopamine D3 receptor activation in the rat in vivo and their modulation by the selective antagonist, (+)-S 14297: 1. Activation of postsynaptic D3 receptors mediates hypothermia, whereas blockade of D2 receptors elicits prolactin secretion and catalepsy
    • Millan, M. J.; Peglion, J. L.; Vian, J.; Rivet, J. M.; Brocco, M.; Gobert, A.; Newman Tancredi, A.; Dacquet, C.; Bervoets, K.; Girardon, S.; Jacques, V.; Chaput, C.; Audinot, V. Functional correlates of dopamine D3 receptor activation in the rat in vivo and their modulation by the selective antagonist, (+)-S 14297: 1. Activation of postsynaptic D3 receptors mediates hypothermia, whereas blockade of D2 receptors elicits prolactin secretion and catalepsy. J. Pharmacol. Exp. Ther. 1995, 275, 885-898.
    • (1995) J. Pharmacol. Exp. Ther. , vol.275 , pp. 885-898
    • Millan, M.J.1    Peglion, J.L.2    Vian, J.3    Rivet, J.M.4    Brocco, M.5    Gobert, A.6    Newman Tancredi, A.7    Dacquet, C.8    Bervoets, K.9    Girardon, S.10    Jacques, V.11    Chaput, C.12    Audinot, V.13
  • 15
    • 0030609852 scopus 로고    scopus 로고
    • 3 receptor agonist, R(+)-7-hydroxy-N,N-di-n-propyl-2-aminotetralin, on memory processes in mice
    • 3 Receptor Agonist, R(+)-7-Hydroxy-N,N-di-n-propyl-2-aminotetralin, on Memory Processes in Mice. Eur. J. Pharmacol. 1997, 324, 147-151.
    • (1997) Eur. J. Pharmacol. , vol.324 , pp. 147-151
    • Ukai, M.1    Tanaka, T.2    Kameyama, T.3
  • 16
    • 0022921561 scopus 로고
    • (+)-AJ 76 and (+)-UH 232: Central stimulants acting as preferential dopamine autoreceptor antagonists
    • Svensson, K.; Johansson, A. M.; Magnusson, T.; Carlsson, A. (+)-AJ 76 and (+)-UH 232: central stimulants acting as preferential dopamine autoreceptor antagonists. Naunyn-Schmiedeberg's Arch. Pharmacol. 1986, 334, 234-245.
    • (1986) Naunyn-Schmiedeberg's Arch. Pharmacol. , vol.334 , pp. 234-245
    • Svensson, K.1    Johansson, A.M.2    Magnusson, T.3    Carlsson, A.4
  • 22
  • 24
    • 0017177961 scopus 로고
    • Centrally acting emetics. 10. Rigid dopamine congeners derived from octahydrobenzo[f]quinoline
    • Cannon, J. G.; Hatheway, G. J. Centrally acting emetics. 10. Rigid dopamine congeners derived from octahydrobenzo[f]quinoline. J. Med. Chem. 1976, 19, 987-993.
    • (1976) J. Med. Chem. , vol.19 , pp. 987-993
    • Cannon, J.G.1    Hatheway, G.J.2
  • 26
    • 0018906709 scopus 로고
    • Congeners of the beta conformer of dopamine derived from cis- and trans-octahydrobenzo[f]quinoline and trans-octahydrobenzo[g]quinoline
    • Cannon, J. G.; Lee, T.; Goldman, H. D.; Long, J. P.; Flynn, J. R.; Verimer, T.; Costall, B.; Naylor, R. J. Congeners of the beta conformer of dopamine derived from cis- and trans-octahydrobenzo[f]quinoline and trans-octahydrobenzo[g]quinoline. J. Med. Chem. 1980, 23, 1-5.
    • (1980) J. Med. Chem. , vol.23 , pp. 1-5
    • Cannon, J.G.1    Lee, T.2    Goldman, H.D.3    Long, J.P.4    Flynn, J.R.5    Verimer, T.6    Costall, B.7    Naylor, R.J.8
  • 27
    • 0018857275 scopus 로고
    • Conversion of ergolines to hexahydro- and octahydrobenzo[f]-quinolines (depyrroloergolines)
    • Bach, N. J.; Kornfeld, E. C.; Clemens, J. A.; Smalstig, E. B. Conversion of ergolines to hexahydro- and octahydrobenzo[f]-quinolines (depyrroloergolines). J. Med. Chem. 1980, 23, 812-814.
    • (1980) J. Med. Chem. , vol.23 , pp. 812-814
    • Bach, N.J.1    Kornfeld, E.C.2    Clemens, J.A.3    Smalstig, E.B.4
  • 29
    • 0024514947 scopus 로고
    • Synthesis and dopaminergic activity of 2-substituted octahydrobenzo[f]quinolines
    • Craig, J. C.; Torkelson, S. M.; Findell, P. R.; Weiner, R. I. Synthesis and dopaminergic activity of 2-substituted octahydrobenzo[f]quinolines. J. Med. Chem. 1989, 32, 961-968.
    • (1989) J. Med. Chem. , vol.32 , pp. 961-968
    • Craig, J.C.1    Torkelson, S.M.2    Findell, P.R.3    Weiner, R.I.4
  • 30
    • 0022006105 scopus 로고
    • Resolved monophenolic 2-aminotetralins and 1,2,3,4,4a,5,6,10b-octahydrobenzo[f]quinolines: Structural and stereochemical considerations for centrally acting pre- and postsynaptic dopamine-receptor agonists
    • Wikström, H.; Andersson, B.; Sanchez, D.; Lindberg, P.; Arvidsson, L. E.; Johansson, A. M.; Nilsson, J. L.; Svensson, K.; Hjorth, S.; Carlsson, A. Resolved monophenolic 2-aminotetralins and 1,2,3,4,4a,5,6,10b-octahydrobenzo[f]quinolines: structural and stereochemical considerations for centrally acting pre- and postsynaptic dopamine-receptor agonists. J. Med. Chem. 1985, 28, 215-225.
    • (1985) J. Med. Chem. , vol.28 , pp. 215-225
    • Wikström, H.1    Andersson, B.2    Sanchez, D.3    Lindberg, P.4    Arvidsson, L.E.5    Johansson, A.M.6    Nilsson, J.L.7    Svensson, K.8    Hjorth, S.9    Carlsson, A.10
  • 32
    • 0021879322 scopus 로고
    • Synthesis and pharmacological activity of the hexahydro-4H-naphth[1,2b][1,4]-oxazines: A new series of potent dopamine receptor agonists
    • Dijkstra, D.; Hazelhoff, B.; Mulder, T. B. A.; de Vries, J. B.; Wynberg, H.; Horn, A. S. Synthesis and Pharmacological Activity of the Hexahydro-4H-naphth[1,2b][1,4]-oxazines: a New Series of Potent Dopamine Receptor Agonists. Eur. J. Med. Chem. 1985, 20, 247-250.
    • (1985) Eur. J. Med. Chem. , vol.20 , pp. 247-250
    • Dijkstra, D.1    Hazelhoff, B.2    Mulder, T.B.A.3    De Vries, J.B.4    Wynberg, H.5    Horn, A.S.6
  • 34
    • 0025021107 scopus 로고
    • Synthesis and dopamine agonist properties of (+-)-trans-3,4,-4a,10b-tetrahydro-4-propyl-2H,5H-[1]benzopyrano [4,3-b]-1,4-oxazin-9-ol and its enantiomers
    • DeWald, H. A.; Heffner, T. G.; Jaen, J. C.; Lustgarten, D. M.; McPhail, A. T.; Meltzer, L. T.; Pugsley, T. A.; Wise, L. D. Synthesis and dopamine agonist properties of (+-)-trans-3,4,-4a,10b-tetrahydro-4-propyl-2H,5H-[1]benzopyrano [4,3-b]-1,4-oxazin-9-ol and its enantiomers. J. Med. Chem. 1990, 33, 445-450.
    • (1990) J. Med. Chem. , vol.33 , pp. 445-450
    • DeWald, H.A.1    Heffner, T.G.2    Jaen, J.C.3    Lustgarten, D.M.4    McPhail, A.T.5    Meltzer, L.T.6    Pugsley, T.A.7    Wise, L.D.8
  • 36
    • 0028979605 scopus 로고
    • Characterization of binding of [3H]PD 128907, a selective dopamine D3 receptor agonist ligand, to CHO-K1 cells
    • Akunne, H. C.; Towers, P.; Ellis, G. J.; Dijkstra, D.; Wikström, H.; Heffner, T. G.; Wise, L. D.; Pugsley, T. A. Characterization of binding of [3H]PD 128907, a selective dopamine D3 receptor agonist ligand, to CHO-K1 cells. Life Sci. 1995, 57, 1401-1410.
    • (1995) Life Sci. , vol.57 , pp. 1401-1410
    • Akunne, H.C.1    Towers, P.2    Ellis, G.J.3    Dijkstra, D.4    Wikström, H.5    Heffner, T.G.6    Wise, L.D.7    Pugsley, T.A.8
  • 37
    • 0025995750 scopus 로고
    • Isosterism and bioisosterism in drug design
    • Burger, A. Isosterism and bioisosterism in drug design. Prog. Drug Res. 1991, 37, 287-371.
    • (1991) Prog. Drug Res. , vol.37 , pp. 287-371
    • Burger, A.1
  • 38
    • 7744243992 scopus 로고    scopus 로고
    • Bioisosterism: A rational approach in drug design
    • Patani, G. A.; LaVoie, E. J. Bioisosterism: A Rational Approach in Drug Design. Chem. Rev. 1996, 96, 3147-3176.
    • (1996) Chem. Rev. , vol.96 , pp. 3147-3176
    • Patani, G.A.1    LaVoie, E.J.2
  • 39
    • 0033559918 scopus 로고    scopus 로고
    • Hydrogen bonding, hydrophobic interactions, and failure of the rigid receptor hypothesis
    • Davis, A. M.; Teague, S. J. Hydrogen Bonding, Hydrophobic Interactions, and Failure of the Rigid Receptor Hypothesis. Angew. Chem., Int. Ed. Engl. 1999, 38, 736-749.
    • (1999) Angew. Chem., Int. Ed. Engl. , vol.38 , pp. 736-749
    • Davis, A.M.1    Teague, S.J.2
  • 40
    • 0342728953 scopus 로고    scopus 로고
    • Pallas version 1.2 is commercially available software from CompuDrug Chemistry Ltd. 1994
    • Pallas version 1.2 is commercially available software from CompuDrug Chemistry Ltd.. 1994.
  • 42
    • 2442643506 scopus 로고
    • Identification of organic compounds. I. Chlorosulfonic acid as a reagent for the identification of aryl halides
    • Huntress, E. H.; Carten, F. H. Identification of Organic Compounds. I. Chlorosulfonic Acid as a Reagent for the Identification of Aryl Halides. J. Am. Chem. Soc. 1940, 62, 511-514.
    • (1940) J. Am. Chem. Soc. , vol.62 , pp. 511-514
    • Huntress, E.H.1    Carten, F.H.2
  • 43
    • 2642592978 scopus 로고
    • Thiophenol
    • John Wiley & Sons: New York
    • Adams, R.; Marvel, C. S. Thiophenol. Organic Syntheses; John Wiley & Sons: New York, 1941; Coll. Vol. I, pp 504-506.
    • (1941) Organic Syntheses
    • Adams, R.1    Marvel, C.S.2
  • 44
    • 0342728951 scopus 로고    scopus 로고
    • Adams, R.; Marvel, C. S. Thiophenol. Organic Syntheses; John Wiley & Sons: New York, 1941; Coll. Vol. I, pp 504-506.
    • Coll. , vol.1 , pp. 504-506
  • 45
    • 0000496188 scopus 로고
    • Thioflavanone, Thio-chromanone und -chromonole
    • Arndt, F.; Flemming, W.; Scholz, E.; Löwensohn, V. Thioflavanone, Thio-chromanone und -chromonole. Ber. 1923, 56, 1269-1279.
    • (1923) Ber. , vol.56 , pp. 1269-1279
    • Arndt, F.1    Flemming, W.2    Scholz, E.3    Löwensohn, V.4
  • 47
    • 0023205265 scopus 로고
    • Practical enantioselective synthesis of a homotyrosine derivative and (R,R)-4-propyl-9-hydroxynaphthoxazine, a potent dopamine agonist
    • Melillo, D. G.; Larsen, R. D.; Mathre, D. J.; Shukis, W. F.; Wood, A. W.; Colleluori, J. R. Practical Enantioselective Synthesis of a Homotyrosine Derivative and (R,R)-4-Propyl-9-hydroxynaphthoxazine, a Potent Dopamine Agonist. J. Org. Chem. 1987, 52, 5143-5150.
    • (1987) J. Org. Chem. , vol.52 , pp. 5143-5150
    • Melillo, D.G.1    Larsen, R.D.2    Mathre, D.J.3    Shukis, W.F.4    Wood, A.W.5    Colleluori, J.R.6
  • 48
    • 0027723678 scopus 로고
    • D2 dopamine receptor stimulation of mitogenesis in transfected chinese hamster ovary cells: Relationship to dopamine stimulation of tyrosine phosphorylations
    • Lajiness, M. E.; Chio, C. L.; Huff, R. M. D2 dopamine receptor stimulation of mitogenesis in transfected Chinese hamster ovary cells: relationship to dopamine stimulation of tyrosine phosphorylations. J. Pharmacol. Exp. Ther. 1993, 267, 1573-1581.
    • (1993) J. Pharmacol. Exp. Ther. , vol.267 , pp. 1573-1581
    • Lajiness, M.E.1    Chio, C.L.2    Huff, R.M.3
  • 49
    • 0028012102 scopus 로고
    • Activation of heterologously expressed D3 dopamine receptors: Comparison with D2 dopamine receptors
    • Chio, C. L.; Lajiness, M. E.; Huff, R. M. Activation of heterologously expressed D3 dopamine receptors: comparison with D2 dopamine receptors. Mol. Pharmacol. 1994, 45, 51-60.
    • (1994) Mol. Pharmacol. , vol.45 , pp. 51-60
    • Chio, C.L.1    Lajiness, M.E.2    Huff, R.M.3
  • 50
    • 0029090618 scopus 로고
    • Effects of putative dopamine D3 receptor agonists, 7-OH-DPAT, and quinpirole, on yawning, stereotypy, and body temperature in rats
    • Kurashima, M.; Yamada, K.; Nagashima, M.; Shirakawa, K.; Furukawa, T. Effects of putative dopamine D3 receptor agonists, 7-OH-DPAT, and quinpirole, on yawning, stereotypy, and body temperature in rats. Pharmacol. Biochem. Behav. 1995, 52, 503-508.
    • (1995) Pharmacol. Biochem. Behav. , vol.52 , pp. 503-508
    • Kurashima, M.1    Yamada, K.2    Nagashima, M.3    Shirakawa, K.4    Furukawa, T.5
  • 51
    • 0015184103 scopus 로고
    • Postsynaptic supersensitivity after 6-hydroxydopamine induced degeneration of the nigro-striatal dopamine system
    • Ungerstedt, U. Postsynaptic supersensitivity after 6-hydroxydopamine induced degeneration of the nigro-striatal dopamine system. Acta Physiol Scand. Suppl. 1971, 367, 69-93.
    • (1971) Acta Physiol Scand. Suppl. , vol.367 , pp. 69-93
    • Ungerstedt, U.1
  • 52
    • 0014954436 scopus 로고
    • Quantitative recording of rotational behavior in rats after 6-hydroxy-doparaine lesions of the nigrostriatal dopamine system
    • Ungerstedt, U.; Arbuthnott, G. W. Quantitative recording of rotational behavior in rats after 6-hydroxy-doparaine lesions of the nigrostriatal dopamine system. Brain Res. 1970, 24, 485-493.
    • (1970) Brain Res. , vol.24 , pp. 485-493
    • Ungerstedt, U.1    Arbuthnott, G.W.2
  • 53
    • 0020736746 scopus 로고
    • Electronegativity and bond energy
    • Sanderson, R. T. Electronegativity and Bond Energy. J. Am. Chem. Soc. 1983, 105, 2259-2261.
    • (1983) J. Am. Chem. Soc. , vol.105 , pp. 2259-2261
    • Sanderson, R.T.1
  • 54
    • 0032484949 scopus 로고    scopus 로고
    • The neuropharmacology of Yawning
    • Argiolas, A.; Melis, M. R. The Neuropharmacology of Yawning. Eur. J. Pharmacol. 1998, 343, 1-16.
    • (1998) Eur. J. Pharmacol. , vol.343 , pp. 1-16
    • Argiolas, A.1    Melis, M.R.2
  • 56
    • 0026863974 scopus 로고
    • Monitoring molecules in the conscious brain by microdialysis
    • Westerink, B. H. C. Monitoring Molecules in the Conscious Brain by Microdialysis. Trends Anal. Chem. 1992, 11, 176-182.
    • (1992) Trends Anal. Chem. , vol.11 , pp. 176-182
    • Westerink, B.H.C.1


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