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Volumn 40, Issue 6, 1997, Pages 858-863

Synthesis, dopamine transporter affinity, dopamine uptake inhibition, and locomotor stimulant activity of 2-substituted 3β-phenyltropane derivatives

Author keywords

[No Author keywords available]

Indexed keywords

3BETA (4 FLUOROPHENYL) 2BETA TROPANECARBOXYLIC ACID METHYL ESTER; 3BETA PHENYLTROPANE; COCAINE; DOPAMINE TRANSPORTER; DOPAMINE UPTAKE INHIBITOR; DRUG CARRIER; SODIUM CHLORIDE; TROPANE DERIVATIVE; TROPARIL; UNCLASSIFIED DRUG;

EID: 0030896771     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm960739c     Document Type: Article
Times cited : (29)

References (31)
  • 1
    • 0026566383 scopus 로고
    • Cocaine receptor: Biochemical characterization and structure-activity relationships of cocaine analogues at the dopamine transporter
    • Carroll, F. I.; Lewin, A. H.; Boja, J. W.; Kuhar, M. J. Cocaine receptor: Biochemical characterization and structure-activity relationships of cocaine analogues at the dopamine transporter. J. Med. Chem. 1992, 35, 969-981.
    • (1992) J. Med. Chem. , vol.35 , pp. 969-981
    • Carroll, F.I.1    Lewin, A.H.2    Boja, J.W.3    Kuhar, M.J.4
  • 2
    • 0026542607 scopus 로고
    • 2β-Substituted analogues of cocaine. Synthesis and inhibition of binding to the cocaine receptor
    • Lewin, A. H.; Gao, Y.; Abraham, P.; Boja, J. W.; Kuhar, M. J.; Carroll, F. I. 2β-Substituted analogues of cocaine. Synthesis and inhibition of binding to the cocaine receptor. J. Med. Chem. 1992, 35, 135-140.
    • (1992) J. Med. Chem. , vol.35 , pp. 135-140
    • Lewin, A.H.1    Gao, Y.2    Abraham, P.3    Boja, J.W.4    Kuhar, M.J.5    Carroll, F.I.6
  • 3
    • 0027064877 scopus 로고
    • Structure-activity relationship studies of cocaine: Replacement of the C-2 ester group by vinyl argues against H-bonding and provides an esterase-resistant high-affinity cocaine analogue
    • Kozikowski, A. P.; Roberti, M.; Xiang, L.; Bergmann, J. S.; Callahan, P. M.; Cunningham, K. A.; Johnson, K. M. Structure-activity relationship studies of cocaine: Replacement of the C-2 ester group by vinyl argues against H-bonding and provides an esterase-resistant high-affinity cocaine analogue. J. Med. Chem. 1992, 35, 4764-4766.
    • (1992) J. Med. Chem. , vol.35 , pp. 4764-4766
    • Kozikowski, A.P.1    Roberti, M.2    Xiang, L.3    Bergmann, J.S.4    Callahan, P.M.5    Cunningham, K.A.6    Johnson, K.M.7
  • 4
    • 0027278546 scopus 로고
    • SAR of cocaine: Further exploration of structural variations at the C-2 center provides compounds of subnanomolar binding potency
    • Kozikowski, A. P.; Roberti, M.; Johnson, K. M.; Bergmann, J. S.; Bale, R. G. SAR of cocaine: Further exploration of structural variations at the C-2 center provides compounds of subnanomolar binding potency. Bioorg. Med. Chem. Lett. 1993, 3, 1327-1332.
    • (1993) Bioorg. Med. Chem. Lett. , vol.3 , pp. 1327-1332
    • Kozikowski, A.P.1    Roberti, M.2    Johnson, K.M.3    Bergmann, J.S.4    Bale, R.G.5
  • 5
    • 0027446171 scopus 로고
    • Novel 2-substituted cocaine analogs: Binding properties at dopamine transporter sites in rat striatum
    • Davies, H. M. L.; Saikali, E.; Sexton, T.; Childers, S. R. Novel 2-substituted cocaine analogs: Binding properties at dopamine transporter sites in rat striatum. Eur. J. Pharmacol. - Mol. Pharmacol. Sect. 1993, 244, 93-97.
    • (1993) Eur. J. Pharmacol. - Mol. Pharmacol. Sect. , vol.244 , pp. 93-97
    • Davies, H.M.L.1    Saikali, E.2    Sexton, T.3    Childers, S.R.4
  • 6
    • 0027363641 scopus 로고
    • 3-Aryl-2-(3′-substituted-1′,2′,4′-oxadiazol- 5′-yl) tropane analogues of cocaine: Affinities at the cocaine binding site at the dopamine, serotonin and norepinephrine transporters
    • Carroll, F. I.; Gray, J. L.; Abraham, P.; Kuzemko, M. A.; Lewin, A. H.; Boja, J. W.; Kuhar, M. J. 3-Aryl-2-(3′-substituted-1′,2′,4′-oxadiazol-5′-yl) tropane analogues of cocaine: Affinities at the cocaine binding site at the dopamine, serotonin and norepinephrine transporters. J. Med. Chem. 1993, 36, 2886-2890.
    • (1993) J. Med. Chem. , vol.36 , pp. 2886-2890
    • Carroll, F.I.1    Gray, J.L.2    Abraham, P.3    Kuzemko, M.A.4    Lewin, A.H.5    Boja, J.W.6    Kuhar, M.J.7
  • 7
    • 0028237668 scopus 로고
    • Synthesis of 2β-acyl-3β-aryl-8-azabicyclo[3.2.1]octanes and their binding affinities at dopamine and serotonin transport sites in rat striatum and frontal cortex
    • Davies, H. M. L.; Saikali, E.; Huby, N. J. S.: Gilliatt, V. J.; Matasi, J. J.; Sexton, T.; Childers, S. R. Synthesis of 2β-acyl-3β-aryl-8-azabicyclo[3.2.1]octanes and their binding affinities at dopamine and serotonin transport sites in rat striatum and frontal cortex. J. Med. Chem. 1994, 37, 1262-1268.
    • (1994) J. Med. Chem. , vol.37 , pp. 1262-1268
    • Davies, H.M.L.1    Saikali, E.2    Huby, N.J.S.3    Gilliatt, V.J.4    Matasi, J.J.5    Sexton, T.6    Childers, S.R.7
  • 8
    • 0027987234 scopus 로고
    • Synthesis, cocaine receptor affinity and dopmaine uptake inhibition of several new 2β-substituted-3β-phenyltropanes
    • Kelkar, S. V.; Izenwasser, S.; Katz, J. L.; Klein, C. L.; Zhu, N.; Trudell, M. L. Synthesis, cocaine receptor affinity and dopmaine uptake inhibition of several new 2β-substituted-3β-phenyltropanes. J. Med. Chem. 1994, 37, 3875-3877.
    • (1994) J. Med. Chem. , vol.37 , pp. 3875-3877
    • Kelkar, S.V.1    Izenwasser, S.2    Katz, J.L.3    Klein, C.L.4    Zhu, N.5    Trudell, M.L.6
  • 9
    • 0029063953 scopus 로고
    • Cocaine and 3β(4′-substituted phenyl)tropane-2β-carboxylic acid ester and amide analogues. New high affinity and selective compounds for the dopamine transporter
    • Carroll, F. I.; Kotian, P.; Dehghani, A.; Gray, J. L.; Kuzemko, M. A.; Parham, K. A.; Abraham, P.; Lewin, A. H.; Boja, J. W.; Kuhar, M. J. Cocaine and 3β(4′-substituted phenyl)tropane-2β-carboxylic acid ester and amide analogues. New high affinity and selective compounds for the dopamine transporter. J. Med. Chem. 1995, 38, 379-388.
    • (1995) J. Med. Chem. , vol.38 , pp. 379-388
    • Carroll, F.I.1    Kotian, P.2    Dehghani, A.3    Gray, J.L.4    Kuzemko, M.A.5    Parham, K.A.6    Abraham, P.7    Lewin, A.H.8    Boja, J.W.9    Kuhar, M.J.10
  • 10
    • 0029122828 scopus 로고
    • Chemistry and biology of the 2β-alkyl-3β-phenyl analogues of cocaine: Subnanomolar affinity ligands that suggest new pharmacophore model at the C-2 position
    • Kozikowski, A. P.; Saiah, M. K. E.; Johnson, K. M.; Bergmann, J. S. Chemistry and biology of the 2β-alkyl-3β-phenyl analogues of cocaine: Subnanomolar affinity ligands that suggest new pharmacophore model at the C-2 position. J. Med. Chem. 1995, 38, 3086-3093.
    • (1995) J. Med. Chem. , vol.38 , pp. 3086-3093
    • Kozikowski, A.P.1    Saiah, M.K.E.2    Johnson, K.M.3    Bergmann, J.S.4
  • 12
    • 0029899173 scopus 로고    scopus 로고
    • Synthesis, ligand binding and quantitative structure-activity relationship study of 3β-(4′-substituted phenyl)-2β-heterocyclic tropanes: Evidence for an electrostatic interaction at the 2β-position
    • Kotian, P.; Muscarella, S. W.; Abraham, P.; Lewin, A. H.; Boja, J. W.; Kuhar, M. J.; Carroll, F. I. Synthesis, ligand binding and quantitative structure-activity relationship study of 3β-(4′-substituted phenyl)-2β-heterocyclic tropanes: Evidence for an electrostatic interaction at the 2β-position. J. Med. Chem. 1996, 39, 2753-2763.
    • (1996) J. Med. Chem. , vol.39 , pp. 2753-2763
    • Kotian, P.1    Muscarella, S.W.2    Abraham, P.3    Lewin, A.H.4    Boja, J.W.5    Kuhar, M.J.6    Carroll, F.I.7
  • 13
    • 0023265754 scopus 로고
    • Cocaine receptors on dopamine transporters are related to self-administration of cocaine
    • Ritz, M. C.; Lamb, R. J.; Goldberg, S. R.; Kuhar, M. Cocaine receptors on dopamine transporters are related to self-administration of cocaine. Science 1987, 237, 1219-1223.
    • (1987) Science , vol.237 , pp. 1219-1223
    • Ritz, M.C.1    Lamb, R.J.2    Goldberg, S.R.3    Kuhar, M.4
  • 14
    • 0023632425 scopus 로고
    • 3H]cocaine in striatum and its relationship to the dopamine transporter
    • 3H]cocaine in striatum and its relationship to the dopamine transporter. Membr. Biochem. 1988, 7, 87-106.
    • (1988) Membr. Biochem. , vol.7 , pp. 87-106
    • Calligaro, D.O.1    Elderfrawi, M.E.2
  • 15
    • 0025855256 scopus 로고
    • The dopamine hypothesis of the reinforcing properties of cocaine
    • Kuhar, M. J.; Ritz, M. C.; Boja, J. W. The dopamine hypothesis of the reinforcing properties of cocaine. Trends Neurosci. 1991, 14, 299-302.
    • (1991) Trends Neurosci. , vol.14 , pp. 299-302
    • Kuhar, M.J.1    Ritz, M.C.2    Boja, J.W.3
  • 16
    • 0027305458 scopus 로고
    • The neural basis of drug craving: An incentive-sensitization theory of addiction
    • Robinson, I.; Barridge, K. C. The neural basis of drug craving: An incentive-sensitization theory of addiction. Brain Res. Rev. 1993, 18, 247-291.
    • (1993) Brain Res. Rev. , vol.18 , pp. 247-291
    • Robinson, I.1    Barridge, K.C.2
  • 18
    • 0030483653 scopus 로고    scopus 로고
    • Stereoselective synthesis of 2β-carbomethoxy-3β-phenyltropane derivatives. Enhanced stereoselectivity observed for the conjugate addition reaction of phenyl-magnesium bromide derivatives with anhydroecgonine methyl ester in dichloromethane
    • Xu, L.; Trudell, M. L. Stereoselective synthesis of 2β-carbomethoxy-3β-phenyltropane derivatives. Enhanced stereoselectivity observed for the conjugate addition reaction of phenyl-magnesium bromide derivatives with anhydroecgonine methyl ester in dichloromethane. J. Heterocycl. Chem. 1996, 33, 2037-2039.
    • (1996) J. Heterocycl. Chem. , vol.33 , pp. 2037-2039
    • Xu, L.1    Trudell, M.L.2
  • 19
    • 0028037643 scopus 로고
    • Differential relationships among dopamine transporter affinities and stimulant potencies of various uptake inhibitors
    • Izenwasser, S.; Terry, P.; Heller, B.; Witkin, J. M.; Katz, J. L. Differential relationships among dopamine transporter affinities and stimulant potencies of various uptake inhibitors. Eur. J. Pharmacol. 1994, 263, 277-283.
    • (1994) Eur. J. Pharmacol. , vol.263 , pp. 277-283
    • Izenwasser, S.1    Terry, P.2    Heller, B.3    Witkin, J.M.4    Katz, J.L.5
  • 20
    • 84920293096 scopus 로고    scopus 로고
    • note
    • The stimulated locomotor activity of 4, 6, and 7 was provided by the NIDA Cocaine Treatment Development Program (CTDP). The analysis of the data was conducted as described in ref 19.
  • 21
    • 0028113212 scopus 로고
    • Pharmacological characterization of the novel discriminative stimulus effects of a low dose of cocaine
    • Terry, P.; Witkin, J. M.; Katz, J. L. Pharmacological characterization of the novel discriminative stimulus effects of a low dose of cocaine. J. Pharmacol. Exp. Ther. 1994, 270, 1041-1048.
    • (1994) J. Pharmacol. Exp. Ther. , vol.270 , pp. 1041-1048
    • Terry, P.1    Witkin, J.M.2    Katz, J.L.3
  • 22
    • 84920293095 scopus 로고    scopus 로고
    • note
    • The drug discrimination activity of 4 was provided by the NIDA CTDP (NIDA contract No. N01DA-2-9305, Assessment of Potential Cocaine Treatment Medications in Rodents, University of Texas Health Science Center, Ft. Worth, TX).
  • 23
    • 84920293094 scopus 로고    scopus 로고
    • note
    • The clogP values were obtained using the Biobyte module within the SYBYL software package. SYBYL 6.2 (Tripose Associates Inc., 1899 S. Hanley Rd., Suite 303, St. Louis, MO 63144-2913, version 6.2 R4000) installed on a Silicon Graphics IRIS Indigo XZ Workstation running IRDC 5.3. Structures were sketched and minimized in SYBYL (BFGS algorithm) which were submitted to MOPAC (version 6.0) for AM1 full geometry optimization and charge calculation.
  • 24
    • 0027131603 scopus 로고
    • Analysis of cocaine receptor site ligand binding bv three-dimensional Voronoi site modeling approach
    • Srivastava, S.; Crippen, G. M. Analysis of cocaine receptor site ligand binding bv three-dimensional Voronoi site modeling approach. J. Med. Chem. 1993, 36, 3572-3579.
    • (1993) J. Med. Chem. , vol.36 , pp. 3572-3579
    • Srivastava, S.1    Crippen, G.M.2
  • 25
    • 0028077861 scopus 로고
    • Conformational aqueous solution and pKa contributions to the binding and activity of cocaine, WIN32 065-2, and the WIN Vinyl analog
    • Yang, B.; Wright, J.; Eldefrawi, M. E.; Pou, S.; MacKerell, A. D., Jr. Conformational aqueous solution and pKa contributions to the binding and activity of cocaine, WIN32 065-2, and the WIN Vinyl analog. J. Am. Chem. Soc. 1994, 116, 8722-8732.
    • (1994) J. Am. Chem. Soc. , vol.116 , pp. 8722-8732
    • Yang, B.1    Wright, J.2    Eldefrawi, M.E.3    Pou, S.4    MacKerell Jr., A.D.5
  • 26
    • 84920293093 scopus 로고    scopus 로고
    • Relations between heterogeneity of dopamine transporter binding and function and the behavioral pharmacology of cocaine
    • in press
    • Katz, J. L.; Newman, A.-H.; Izenwasser, S. Relations between heterogeneity of dopamine transporter binding and function and the behavioral pharmacology of cocaine. Pharmacol. Biochem. Behav., in press.
    • Pharmacol. Biochem. Behav.
    • Katz, J.L.1    Newman, A.-H.2    Izenwasser, S.3
  • 27
    • 0019219948 scopus 로고
    • Aryl 1,4-dialk(en)ylpiperazines as selective and very potent inhibitors of dopamine uptake
    • van der Zee, P.; Koger, H. S.; Gootjes, J.; Hespe, W. Aryl 1,4-dialk(en)ylpiperazines as selective and very potent inhibitors of dopamine uptake. Eur. J. Med. Chem. 1980, 15, 363-370.
    • (1980) Eur. J. Med. Chem. , vol.15 , pp. 363-370
    • Van Der Zee, P.1    Koger, H.S.2    Gootjes, J.3    Hespe, W.4
  • 28
    • 0027139321 scopus 로고
    • Methoxylation of cocaine reduces binding affinity and produces compounds of differential binding and dopamine uptake inhibitory activity: Discovery of a weak cocaine "antagonist"
    • Simoni, D.; Stoelwinder, J.; Kozikowski, A. P.; Johnson, K. M.; Bergmann, J. S.; Ball, R. G. Methoxylation of cocaine reduces binding affinity and produces compounds of differential binding and dopamine uptake inhibitory activity: Discovery of a weak cocaine "antagonist". J. Med. Chem. 1993, 36, 3975-3977.
    • (1993) J. Med. Chem. , vol.36 , pp. 3975-3977
    • Simoni, D.1    Stoelwinder, J.2    Kozikowski, A.P.3    Johnson, K.M.4    Bergmann, J.S.5    Ball, R.G.6
  • 29
    • 0028133248 scopus 로고
    • The discovery of an unusually selective and novel cocaine analog: Difluoropine. Synthesis and inhibition of binding at cocaine recognition sites
    • Meltzer, P. C.; Liang, A. Y.; Madras, B. K. The discovery of an unusually selective and novel cocaine analog: Difluoropine. Synthesis and inhibition of binding at cocaine recognition sites. J. Med. Chem. 1994, 37, 2001-2010.
    • (1994) J. Med. Chem. , vol.37 , pp. 2001-2010
    • Meltzer, P.C.1    Liang, A.Y.2    Madras, B.K.3
  • 30
    • 0028804967 scopus 로고
    • Novel 4′-substituted and 4′,4″-disubstituted-3α-(Diphenylmethoxy)tropane analogs as potent and selective dopamine uptake inhibitors
    • Newman, A.-H.; Kline, R. H.; Allen, A. C.; Izenwasser, S.; George, C.; Katz, J. L. Novel 4′-substituted and 4′,4″-disubstituted-3α-(Diphenylmethoxy)tropane analogs as potent and selective dopamine uptake inhibitors. J. Med. Chem. 1995, 38, 3933-3940.
    • (1995) J. Med. Chem. , vol.38 , pp. 3933-3940
    • Newman, A.-H.1    Kline, R.H.2    Allen, A.C.3    Izenwasser, S.4    George, C.5    Katz, J.L.6
  • 31
    • 0004279229 scopus 로고
    • Brooks/Cole Publishing Co.: Pacific Grove, CA
    • Kirk, R. E. Experimental Design, 2nd ed.; Brooks/Cole Publishing Co.: Pacific Grove, CA, 1982; pp 119-120.
    • (1982) Experimental Design, 2nd Ed. , pp. 119-120
    • Kirk, R.E.1


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