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Volumn 8, Issue 8, 1996, Pages 531-544

Synthesis and pharmacology of the enantiomers of UH301: Opposing interactions with 5-HT1A receptors

Author keywords

5 HT1A receptor antagonists; Enantiomers; Rat biochemistry; UH301

Indexed keywords

2 DIPROPYLAMINO 5 FLUORO 8 HYDROXYTETRALIN; SEROTONIN RECEPTOR;

EID: 3242855090     PISSN: 08990042     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1520-636X(1996)8:8<531::AID-CHIR1>3.0.CO;2-C     Document Type: Article
Times cited : (3)

References (70)
  • 1
    • 3242863693 scopus 로고    scopus 로고
    • 1996 Receptor & ion channel nomenclature supplement ISNN 1357 485X
    • For a recent overview of serotonin (5-HT) receptors see: 1996 Receptor & ion channel nomenclature supplement ISNN 1357 485X. Trends Pharmacol. Sci. 1996.
    • (1996) Trends Pharmacol. Sci.
  • 11
    • 0028121008 scopus 로고
    • The effects of WAY-100135 and 8-hydroxy-2-(di-n-propylamino)tetralin on feeding in the rat
    • e) Hartley, J., Fletcher, A. The effects of WAY-100135 and 8-hydroxy-2-(di-n-propylamino)tetralin on feeding in the rat. Eur. J. Pharmacol. 252:329-332, 1994.
    • (1994) Eur. J. Pharmacol. , vol.252 , pp. 329-332
    • Hartley, J.1    Fletcher, A.2
  • 12
    • 0028111617 scopus 로고
    • 1A receptor antagonist, in the murine elevated plusmaze test
    • 1A receptor antagonist, in the murine elevated plusmaze test. Eur. J. Pharmacol. 261:321-325, 1994.
    • (1994) Eur. J. Pharmacol. , vol.261 , pp. 321-325
    • Rodgers, R.J.1    Cole, J.C.2
  • 16
    • 0028926033 scopus 로고
    • 1A receptor antagonist
    • 1A receptor antagonist. Brain Res. 673:217-225, 1995.
    • (1995) Brain Res. , vol.673 , pp. 217-225
    • Khawaja, X.1
  • 20
    • 0025756714 scopus 로고
    • (S)-UH-301 antagonizes (R)-8-OH DPAT-induced cardiovascular effects in the rat
    • a) Björk, L., Lindgren, S., Hacksell, U., Lewander, T. (S)-UH-301 antagonizes (R)-8-OH DPAT-induced cardiovascular effects in the rat. Eur. J. Pharmacol. 199:367-370, 1991.
    • (1991) Eur. J. Pharmacol. , vol.199 , pp. 367-370
    • Björk, L.1    Lindgren, S.2    Hacksell, U.3    Lewander, T.4
  • 21
    • 0025785785 scopus 로고
    • Pharmacology of the novel 5-HT1A-receptor antagonist (S)-5-fluoro-8-hydroxy-2-(dipropylamino)tetralin, (S)-UH-301: Inhibition of (R)-8-OH DPAT-induced effects
    • b) Björk, L., Cornfield, L.J., Nelson, D.L., Hillver, S.-E., Anden, N.-E., Lewander, T., Hacksell, U. Pharmacology of the novel 5-HT1A-receptor antagonist (S)-5-fluoro-8-hydroxy-2-(dipropylamino)tetralin, (S)-UH-301: Inhibition of (R)-8-OH DPAT-induced effects. J. Pharm. Exp. Ther. 258:58-65, 1991.
    • (1991) J. Pharm. Exp. Ther. , vol.258 , pp. 58-65
    • Björk, L.1    Cornfield, L.J.2    Nelson, D.L.3    Hillver, S.-E.4    Anden, N.-E.5    Lewander, T.6    Hacksell, U.7
  • 22
    • 0025918403 scopus 로고
    • 1A receptor antagonist (S)-UH-301 antagonizes 8-OH-DPAT-induced effects on male as well as female rat copulatory behaviour
    • 1A receptor antagonist (S)-UH-301 antagonizes 8-OH-DPAT-induced effects on male as well as female rat copulatory behaviour. Eur. J. Pharmacol. 202:81-87, 1991.
    • (1991) Eur. J. Pharmacol. , vol.202 , pp. 81-87
    • Johansson, C.E.1    Meyerson, B.J.2    Hacksell, U.3
  • 23
    • 0026874736 scopus 로고
    • Effects of (R)-8-OH DPAT and the enantiomers of UH-301 on motor activities in the rat. Antagonism of (R)-8-OH DPAT-induced effects
    • d) Björk, L., Fredriksson, A., Hacksell, U., Lewander, T. Effects of (R)-8-OH DPAT and the enantiomers of UH-301 on motor activities in the rat. Antagonism of (R)-8-OH DPAT-induced effects. Eur. Neuropsychopharmacol. 2:141-147, 1992.
    • (1992) Eur. Neuropsychopharmacol. , vol.2 , pp. 141-147
    • Björk, L.1    Fredriksson, A.2    Hacksell, U.3    Lewander, T.4
  • 24
    • 0026616960 scopus 로고
    • 1A receptor antagonist (S)-UH-301 prevents (R)-8-OH-DPAT-induced decrease in interstitial concentrations of serotonin in the rat hippocampus
    • 1A receptor antagonist (S)-UH-301 prevents (R)-8-OH-DPAT-induced decrease in interstitial concentrations of serotonin in the rat hippocampus. Eur. J. Pharmacol. 216:373-378, 1992.
    • (1992) Eur. J. Pharmacol. , vol.216 , pp. 373-378
    • Nomikos, G.G.1    Arborelius, L.2    Svensson, T.H.3
  • 27
    • 0027975125 scopus 로고
    • 1A receptor antagonist (S)-UH-301 blocks the (R)-8-OH-DPAT-induced inhibition of serotonergic dorsal raphe cell firing in the rat
    • 1A receptor antagonist (S)-UH-301 blocks the (R)-8-OH-DPAT-induced inhibition of serotonergic dorsal raphe cell firing in the rat. J. Neural Transm. Gen. Sect. 96:179-186, 1994.
    • (1994) J. Neural Transm. Gen. Sect. , vol.96 , pp. 179-186
    • Arborelius, L.1    Backlund Hook, B.2    Hacksell, U.3    Svensson, T.H.4
  • 31
    • 0020367109 scopus 로고
    • 8-Hydroxy-2-(di-n-propylamino)tetralin, 8-OH-DPAT, a potent and selective simplified ergot congener with central 5-HT-receptor stimulating activity
    • b) Hjorth, S., Carlsson, A., Lindberg, P., Sanchez, D., Wikstrom, H., Arvidsson, L.-E., Hacksell, U., Nilsson, J.L.G. 8-Hydroxy-2-(di-n-propylamino)tetralin, 8-OH-DPAT, a potent and selective simplified ergot congener with central 5-HT-receptor stimulating activity. J. Neural Transm. 55:169-188, 1982.
    • (1982) J. Neural Transm. , vol.55 , pp. 169-188
    • Hjorth, S.1    Carlsson, A.2    Lindberg, P.3    Sanchez, D.4    Wikstrom, H.5    Arvidsson, L.-E.6    Hacksell, U.7    Nilsson, J.L.G.8
  • 33
    • 0025767882 scopus 로고
    • Intrinsic activity of enantiomers of 8-hydroxy-2-(di-n-propylamino)tetralin and its analogues at 5-hydroxytryptamine1A receptors that are negatively coupled to adenylate cyclase
    • d) Cornfield. L.J., Lambert, G., Arvidsson, L-E., Mellin, C., Vallgårda, J., Hacksell, U., Nelson, D.L. Intrinsic activity of enantiomers of 8-hydroxy-2-(di-n-propylamino)tetralin and its analogues at 5-hydroxytryptamine1A receptors that are negatively coupled to adenylate cyclase. Mol. Pharmacol. 39:780-787, 1991.
    • (1991) Mol. Pharmacol. , vol.39 , pp. 780-787
    • Cornfield, L.J.1    Lambert, G.2    Arvidsson, L.-E.3    Mellin, C.4    Vallgårda, J.5    Hacksell, U.6    Nelson, D.L.7
  • 34
    • 0027199189 scopus 로고
    • (R)-8-OH-DPAT preferentially increases dopamine release in rat medial prefrontal cortex
    • e) Arborelius, L., Nomikos, G.G., Hacksell, U., Svensson, T.H. (R)-8-OH-DPAT preferentially increases dopamine release in rat medial prefrontal cortex. Acta. Physiol. Scand. 148:465-466, 1993.
    • (1993) Acta. Physiol. Scand. , vol.148 , pp. 465-466
    • Arborelius, L.1    Nomikos, G.G.2    Hacksell, U.3    Svensson, T.H.4
  • 35
    • 0027163303 scopus 로고
    • 5-HT and antidepressants: New views from microdialysis studies
    • a) Artigas, F. 5-HT and antidepressants: New views from microdialysis studies. Trends Pharmacol. Sci. 14:262, 1993.
    • (1993) Trends Pharmacol. Sci. , vol.14 , pp. 262
    • Artigas, F.1
  • 37
    • 0027339127 scopus 로고
    • 1A autoreceptor blockade potentiates the ability of the 5-HT reuptake inhibitor citalopram to increase nerve terminal output of 5-HT in vivo: A microdialysis study
    • 1A autoreceptor blockade potentiates the ability of the 5-HT reuptake inhibitor citalopram to increase nerve terminal output of 5-HT in vivo: a microdialysis study. J. Neurochem. 60:776-779, 1993.
    • (1993) J. Neurochem. , vol.60 , pp. 776-779
    • Hjorth, S.1
  • 38
    • 0028287265 scopus 로고
    • Current advances and trends in the treatment of depression
    • d) Blier, P., de Montigny, C. Current advances and trends in the treatment of depression. Trends Pharmacol. Sci. 15:220-226, 1994.
    • (1994) Trends Pharmacol. Sci. , vol.15 , pp. 220-226
    • Blier, P.1    De Montigny, C.2
  • 39
    • 0028170297 scopus 로고
    • 1A autoreceptors in the action of selective serotonin reuptake inhibitors
    • 1A autoreceptors in the action of selective serotonin reuptake inhibitors. Eur. J. Pharmacol. 260:251-255, 1994.
    • (1994) Eur. J. Pharmacol. , vol.260 , pp. 251-255
    • Hjorth, S.1    Auerbach, S.B.2
  • 41
    • 0001590919 scopus 로고
    • Preparation of aromatic fluorine compounds from diazonium fluoborates
    • a) Roe, A. Preparation of aromatic fluorine compounds from diazonium fluoborates. Org. Reaction 5:193-228, 1949.
    • (1949) Org. Reaction , vol.5 , pp. 193-228
    • Roe, A.1
  • 42
    • 84889101918 scopus 로고
    • George Thieme Verlag, Stuttgart
    • b) Houben-Weyl, Methoden der organischen Chemie, George Thieme Verlag, Stuttgart, Vol. 5/3, 1962: 213-246.
    • (1962) Methoden der Organischen Chemie , vol.5 , Issue.3 , pp. 213-246
    • Houben-Weyl1
  • 43
    • 84987265462 scopus 로고
    • Reactions of organic compounds with xenon fluorides
    • Filler, R. Reactions of organic compounds with xenon fluorides. Israel J. Chem. 17:71-90, 1978.
    • (1978) Israel J. Chem. , vol.17 , pp. 71-90
    • Filler, R.1
  • 44
    • 85033167926 scopus 로고
    • ACS Monograph Series No. 87, New York: Reinhold Publishing Corporation
    • Thomas, C.A. Anhydrous Aluminum Chloride. ACS Monograph Series No. 87, New York: Reinhold Publishing Corporation, 1941.
    • (1941) Anhydrous Aluminum Chloride
    • Thomas, C.A.1
  • 45
    • 3242854217 scopus 로고
    • Thallium in organic synthesis. 47. Regioselective ring expansion of cyclic aralkyl ketones via Wittig-derived olefins with tallium(III) nitrate (TTN)
    • Taylor, E.C., Chiang, C.-S., McKillop, A. Thallium in organic synthesis. 47. Regioselective ring expansion of cyclic aralkyl ketones via Wittig-derived olefins with tallium(III) nitrate (TTN). Tetrahedron Lett. 1827-1830, 1977.
    • (1977) Tetrahedron Lett. , pp. 1827-1830
    • Taylor, E.C.1    Chiang, C.-S.2    McKillop, A.3
  • 46
    • 0027243118 scopus 로고
    • Synthesis of (+)-(R)- And (-)-(S)-5-Hydroxy-2-methyl-2-dipropylaminotetralin: Effects on rat hippocampal output of 5-HT, 5-HIAA, and DOPAC as determined by in vivo microdialysis
    • Backlund Höök, B., Johansson, A.M., Hjorth, S., Sundell, S., Hacksell, U. Synthesis of (+)-(R)- and (-)-(S)-5-Hydroxy-2-methyl-2-dipropylaminotetralin: Effects on rat hippocampal output of 5-HT, 5-HIAA, and DOPAC as determined by in vivo microdialysis. Chirality 5:112-119, 1993.
    • (1993) Chirality , vol.5 , pp. 112-119
    • Backlund Höök, B.1    Johansson, A.M.2    Hjorth, S.3    Sundell, S.4    Hacksell, U.5
  • 47
    • 25944455770 scopus 로고
    • Conformational analysis of 2-aminotetralins: Molecular mechanics calculations, X-ray crystallography and nuclear magnetic resonance spectroscopy
    • M
    • Karlén, A., Helander, A., Johansson, A.M., Kenne, L., Sundell, S., Hacksell, U. Conformational analysis of 2-aminotetralins: Molecular mechanics calculations, X-ray crystallography and nuclear magnetic resonance spectroscopy. J. Chem. Res. (S), 448-449, (M), 3028-3036, 1993.
    • (1993) J. Chem. Res. (S) , pp. 448-449
    • Karlén, A.1    Helander, A.2    Johansson, A.M.3    Kenne, L.4    Sundell, S.5    Hacksell, U.6
  • 48
    • 85033164810 scopus 로고    scopus 로고
    • Wavefunction Inc., 18401 Von Karman Ave., Suite 370, Irvine, CA 92715
    • Wavefunction Inc., 18401 Von Karman Ave., Suite 370, Irvine, CA 92715.
  • 49
    • 0023858415 scopus 로고
    • Structural factors of importance for 5-hydroxytryptaminergic activity. Conformational preferences and electrostatic potentials of 8-hydroxy-2-(di-n-propytamino)tetralin (8-OH-DPAT) and some related agents
    • Arvidsson, L.-E., Karlén, Anders, Norinder, U., Kenne, L., Sundell, S., Hacksell, U. Structural factors of importance for 5-hydroxytryptaminergic activity. Conformational preferences and electrostatic potentials of 8-hydroxy-2-(di-n-propytamino)tetralin (8-OH-DPAT) and some related agents. J. Med. Chem. 31:212-221, 1988.
    • (1988) J. Med. Chem. , vol.31 , pp. 212-221
    • Arvidsson, L.-E.1    Karlén, A.2    Norinder, U.3    Kenne, L.4    Sundell, S.5    Hacksell, U.6
  • 51
    • 0022544893 scopus 로고
    • The inhibition of the cage-leaving response - A model for studies of the serotoninergic neurotransmission in the rat
    • Rényi, L., Archer, T., Minor B.G., Tandberg, B., Fredriksson, A., Ross, S.B. The inhibition of the cage-leaving response - a model for studies of the serotoninergic neurotransmission in the rat. J. Neural Transm. 65:193-210, 1986.
    • (1986) J. Neural Transm. , vol.65 , pp. 193-210
    • Rényi, L.1    Archer, T.2    Minor, B.G.3    Tandberg, B.4    Fredriksson, A.5    Ross, S.B.6
  • 52
    • 25944467969 scopus 로고
    • 2 receptors in different components of the 5-HT syndrome in the rat
    • 2 receptors in different components of the 5-HT syndrome in the rat. Neuroscience 22:225P, 1987.
    • (1987) Neuroscience , vol.22
    • Rényi, L.1
  • 56
    • 0000861818 scopus 로고
    • Improved preparation, chromatographic separation and X-ray crystallographic determination of the absolute configuration of the enantiomers of 8-hydroxy-2-(dipropylamino)tetralin (8-OH-DPAT)
    • Karlsson, A., Pettersson, C., Sundell, S., Arvidsson, L.-E., Hacksell, U. Improved preparation, chromatographic separation and X-ray crystallographic determination of the absolute configuration of the enantiomers of 8-hydroxy-2-(dipropylamino)tetralin (8-OH-DPAT). Acta. Chem. Scand. 842:231-236, 1988.
    • (1988) Acta. Chem. Scand. , vol.842 , pp. 231-236
    • Karlsson, A.1    Pettersson, C.2    Sundell, S.3    Arvidsson, L.-E.4    Hacksell, U.5
  • 57
    • 0023552726 scopus 로고
    • Effects of the C3-methylated derivatives of 8-hydroxy-2-(di-n-propylamino)tetratin (8-OH-DPAT) on central 5-hydroxytryptamine receptors
    • a) Björk, L., Mellin, C., Hacksell, U., Andén, N.-E. Effects of the C3-methylated derivatives of 8-hydroxy-2-(di-n-propylamino)tetratin (8-OH-DPAT) on central 5-hydroxytryptamine receptors. Eur. J. Pharmacol. 143:55-63, 1987.
    • (1987) Eur. J. Pharmacol. , vol.143 , pp. 55-63
    • Björk, L.1    Mellin, C.2    Hacksell, U.3    Andén, N.-E.4
  • 58
    • 0023905095 scopus 로고
    • Central dopaminergic and 5-hydroxytryplaminergic effects of C3-methylated derivatives of 8-hydroxy-2-(di-n-propylamino)tetralin
    • b) Mellin, C., Björk, L., Karlén, A., Johansson, A.M., Sundell, S., Kenne, L., Nelson, D.L., Andén, N.-E., Hacksell, U. Central dopaminergic and 5-hydroxytryplaminergic effects of C3-methylated derivatives of 8-hydroxy-2-(di-n-propylamino)tetralin. J. Med. Chem. 31:1130-1140, 1988.
    • (1988) J. Med. Chem. , vol.31 , pp. 1130-1140
    • Mellin, C.1    Björk, L.2    Karlén, A.3    Johansson, A.M.4    Sundell, S.5    Kenne, L.6    Nelson, D.L.7    Andén, N.-E.8    Hacksell, U.9
  • 61
    • 84943920736 scopus 로고
    • Phase annealing in SHELX-90: Direct methods for larger structures
    • Sheldrick, G.M., Phase annealing in SHELX-90: Direct methods for larger structures. Acta. Crystallogr. A46:467-473, 1990.
    • (1990) Acta. Crystallogr. , vol.A46 , pp. 467-473
    • Sheldrick, G.M.1
  • 63
    • 84944643247 scopus 로고
    • updated by D. Rabinovich and K Reich; Department of Structural Chemistry, Weizmann Institute of Science, Rehovot, Israel; and subsequently modified by G.M. Sheldrick, University of Göttingen, Germany
    • b) Sheldrick, G.M., SHELX 400 ATOM VERSION; updated by D. Rabinovich and K Reich; Department of Structural Chemistry, Weizmann Institute of Science, Rehovot, Israel; and subsequently modified by G.M. Sheldrick, University of Göttingen, Germany, 1979.
    • (1979) SHELX 400 Atom Version
    • Sheldrick, G.M.1
  • 64
    • 0001004777 scopus 로고
    • Significance test on the crystallographic R factor
    • Hamilton, W.C., Significance test on the crystallographic R factor. Acta. Crystallogr. 18:502-510, 1965.
    • (1965) Acta. Crystallogr. , vol.18 , pp. 502-510
    • Hamilton, W.C.1
  • 65
    • 84909809091 scopus 로고
    • On the application of Hamilton's ratio test to the assignment of absolute configuration and an alternative test
    • Rogers, D., On the application of Hamilton's ratio test to the assignment of absolute configuration and an alternative test Acta. Crystallogr. A37:734-741, 1981.
    • (1981) Acta. Crystallogr. , vol.A37 , pp. 734-741
    • Rogers, D.1
  • 66
    • 0020909036 scopus 로고
    • PARST: A system of FORTRAN routines for calculating molecular structure parameters from results of crystal structure analyses
    • Nardelli, M. PARST: A system of FORTRAN routines for calculating molecular structure parameters from results of crystal structure analyses. Comput. Chem. 7:95-98, 1983.
    • (1983) Comput. Chem. , vol.7 , pp. 95-98
    • Nardelli, M.1
  • 68
    • 0015440803 scopus 로고
    • Simultaneous measurement of tyrosine and tryptophan hydroxylase activities in brain in vivo using an inhibitor of the aromatic amino acid decarboxylase
    • Carlsson, A., Davis, J.N., Kehr, W., Undqvist, M., Atack, C.V. Simultaneous measurement of tyrosine and tryptophan hydroxylase activities in brain in vivo using an inhibitor of the aromatic amino acid decarboxylase. Naunyn-Schmiedeberg's Arch. Pharmacol. 275:153-168, 1972.
    • (1972) Naunyn-Schmiedeberg's Arch. Pharmacol. , vol.275 , pp. 153-168
    • Carlsson, A.1    Davis, J.N.2    Kehr, W.3    Undqvist, M.4    Atack, C.V.5
  • 70
    • 4644289782 scopus 로고
    • Relativistic calculation of anomalous scattering factors for X-rays
    • Cromer, D.T., Liberman, D. Relativistic calculation of anomalous scattering factors for X-rays. J. Chem. Phys. 53:1891-1899, 1970.
    • (1970) J. Chem. Phys. , vol.53 , pp. 1891-1899
    • Cromer, D.T.1    Liberman, D.2


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