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Volumn 41, Issue 17, 1998, Pages 3293-3297

Tolerance in the replacement of the benzhydrylic O atom in 4-[2- (diphenylmethoxy)ethyl]-1-benzylpiperidine derivatives by an N atom: Development of new-generation potent and selective N-analogue molecules for the dopamine transporter

Author keywords

[No Author keywords available]

Indexed keywords

3BETA (4 FLUOROPHENYL) 2BETA TROPANECARBOXYLIC ACID METHYL ESTER; 4 [2 (DIPHENYLMETHOXY)ETHYL] 1 BENZYLPIPERIDINE DERIVATIVE; 4 [2 [(DIPHENYLMETHYL)AMINO]ETHYL] 1 [(4 FLUOROPHENYL)METHYL]PIPERIDINE; 4 [[[BIS(4 FLUOROPHENYL)METHYL]AMINO]ETHYL] 1 BENZYLPIPERIDINE; BENZHYDRYL DERIVATIVE; CITALOPRAM; COCAINE; DOPAMINE; DOPAMINE TRANSPORTER; NITROGEN; OXYGEN; PIPERIDINE DERIVATIVE; SEROTONIN TRANSPORTER; UNCLASSIFIED DRUG; VANOXERINE;

EID: 0032514388     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm980066t     Document Type: Article
Times cited : (28)

References (31)
  • 1
    • 0026399682 scopus 로고
    • Opium, Cocaine and Marijuana in American History
    • Musto, D. F. Opium, Cocaine and Marijuana in American History. Sci. Am. 1991, 256, 40-47.
    • (1991) Sci. Am. , vol.256 , pp. 40-47
    • Musto, D.F.1
  • 2
    • 0022481325 scopus 로고
    • Structural requirements for cocaine congeners to interact with dopamine and serotonin uptake sites in mouse brain and to induced stereotyped behavior
    • Reith, M. E. A.; Meisler, B. E.; Sershen, H.; Lajtha, A. Structural requirements for cocaine congeners to interact with dopamine and serotonin uptake sites in mouse brain and to induced stereotyped behavior. Biochem. Pharmacol. 1986, 35, 1123-1129.
    • (1986) Biochem. Pharmacol. , vol.35 , pp. 1123-1129
    • Reith, M.E.A.1    Meisler, B.E.2    Sershen, H.3    Lajtha, A.4
  • 3
    • 0025008955 scopus 로고
    • Cocaine inhibition of ligand binding at dopamine, norpinephrine and serotonin transporters: A structure-activity study
    • Ritz, M. C.; Cone, E. J.; Kuhar, M. J. Cocaine inhibition of ligand binding at dopamine, norpinephrine and serotonin transporters: A structure-activity study. Life Sci. 1990, 46, 635-645.
    • (1990) Life Sci. , vol.46 , pp. 635-645
    • Ritz, M.C.1    Cone, E.J.2    Kuhar, M.J.3
  • 4
    • 0023265754 scopus 로고
    • Cocaine receptors on dopamine transporters are related to self-adminstration of cocaine
    • Ritz, M. C.; Lamb, R. J.; Goldberg, R.; Kuhar, M. J. Cocaine receptors on dopamine transporters are related to self-adminstration of cocaine. Science 1987, 237, 1219-1223.
    • (1987) Science , vol.237 , pp. 1219-1223
    • Ritz, M.C.1    Lamb, R.J.2    Goldberg, R.3    Kuhar, M.J.4
  • 5
    • 0030071106 scopus 로고    scopus 로고
    • Hyperlocomotion and indifference to cocaine and amphetamine in mice lacking the dopamine transporter
    • Giros, B.; Jaber, M.; Jones, S. R.; Wightman, R. M.; Caron, M. G. Hyperlocomotion and indifference to cocaine and amphetamine in mice lacking the dopamine transporter. Nature 1996, 379, 606-612.
    • (1996) Nature , vol.379 , pp. 606-612
    • Giros, B.1    Jaber, M.2    Jones, S.R.3    Wightman, R.M.4    Caron, M.G.5
  • 6
    • 0002379639 scopus 로고    scopus 로고
    • Dopamine transporter uptake blockers: Structure activity relationships
    • Reith, M. E. A., Eds.; Human Press: Totowa, NJ
    • Carrol, F. I.; Lewin, A. H.; Kuhar, M. J. Dopamine transporter uptake blockers: Structure activity relationships. In Neurotransmitter Transporters: Structure and Function; Reith, M. E. A., Eds.; Human Press: Totowa, NJ, 1997; 263-295.
    • (1997) Neurotransmitter Transporters: Structure and Function , pp. 263-295
    • Carrol, F.I.1    Lewin, A.H.2    Kuhar, M.J.3
  • 7
    • 0029919127 scopus 로고    scopus 로고
    • Synthesis and pharmacology of potential cocaine antagonists. 2. Structure-activity relationship studies of aromatic ring substituted methylphenidate analogues
    • (a) Deutsch, H. M.; Shi, Q.; Gruszecka-Kowalik, E.; Schweri, M. M. Synthesis and pharmacology of potential cocaine antagonists. 2. Structure-activity relationship studies of aromatic ring substituted methylphenidate analogues. J. Med. Chem. 1996, 39, 1201-1209.
    • (1996) J. Med. Chem. , vol.39 , pp. 1201-1209
    • Deutsch, H.M.1    Shi, Q.2    Gruszecka-Kowalik, E.3    Schweri, M.M.4
  • 8
    • 0031434059 scopus 로고    scopus 로고
    • Novel N-substituted 3α-[bis(4′-fluorophenyl)methoxy]tropane analogues: Selective ligands for the dopamine transporter
    • (b) Agoston, G. E.; Wu, J. H.; Izenwasser, S.; George, C.; Katz, J.; Kline, R. H.; Newman, A-H. Novel N-substituted 3α-[bis(4′-fluorophenyl)methoxy]tropane analogues: selective ligands for the dopamine transporter. J. Med. Chem. 1997, 40, 4329-4339.
    • (1997) J. Med. Chem. , vol.40 , pp. 4329-4339
    • Agoston, G.E.1    Wu, J.H.2    Izenwasser, S.3    George, C.4    Katz, J.5    Kline, R.H.6    Newman, A.-H.7
  • 9
    • 0030837830 scopus 로고    scopus 로고
    • 2-Carbomethoxy-3-aryl-8-oxabicyclo[3.2.1]octanes: Potent non-nitrogen inhibitors of monoamine transporters
    • Meltzer, P. C.; Liang, A. Y.; Blundell, P.; Gonzalez, M. D.; Chen, Z.; George, C.; Madras, B. K. 2-Carbomethoxy-3-aryl-8-oxabicyclo[3.2.1]octanes: Potent non-nitrogen inhibitors of monoamine transporters. J. Med. Chem. 1997, 40, 2661-2673.
    • (1997) J. Med. Chem. , vol.40 , pp. 2661-2673
    • Meltzer, P.C.1    Liang, A.Y.2    Blundell, P.3    Gonzalez, M.D.4    Chen, Z.5    George, C.6    Madras, B.K.7
  • 10
    • 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
  • 11
    • 0023187594 scopus 로고
    • 3H]GBR 12935 binding in vitro to rat striatal membranes: Labeling of the dopamine uptake complex
    • 3H]GBR 12935 binding in vitro to rat striatal membranes: labeling of the dopamine uptake complex. J. Neurochem. 1987, 48, 1887-1896.
    • (1987) J. Neurochem. , vol.48 , pp. 1887-1896
    • Anderson, P.H.1
  • 12
    • 0024960595 scopus 로고
    • The dopamine uptake inhibitor GBR 12909: Selectivity and molecular mechanism of action
    • Anderson, P. H. The dopamine uptake inhibitor GBR 12909: selectivity and molecular mechanism of action. Eur. J. Pharmacol. 1989, 166, 493-504.
    • (1989) Eur. J. Pharmacol. , vol.166 , pp. 493-504
    • Anderson, P.H.1
  • 13
    • 0031055081 scopus 로고    scopus 로고
    • Heteroaromatic analogues of 1-[2-(diphenylmethoxy)ethyl]- and 1-[2-[bis(4-fluorophenyl)methoxy]ethyl]-4-(3-phenylpropyl)piperazines (GBR 12935 and GBR 12909) as high-affinity dopamine reuptake inhibitors
    • Matecka, D.; Lewis, D.; Rothman, R. B.; Dersch, C. M.; Wojnicki, F. H. E.; Glowa, J. R.; DeVries, C.; Pert, A.; Rice, K. C. Heteroaromatic analogues of 1-[2-(diphenylmethoxy)ethyl]- and 1-[2-[bis(4-fluorophenyl)methoxy]ethyl]-4-(3-phenylpropyl)piperazines (GBR 12935 and GBR 12909) as high-affinity dopamine reuptake inhibitors. J. Med. Chem. 1997, 40, 705-716.
    • (1997) J. Med. Chem. , vol.40 , pp. 705-716
    • Matecka, D.1    Lewis, D.2    Rothman, R.B.3    Dersch, C.M.4    Wojnicki, F.H.E.5    Glowa, J.R.6    DeVries, C.7    Pert, A.8    Rice, K.C.9
  • 14
    • 0030473215 scopus 로고    scopus 로고
    • Development of novel, potent, and selective dopamine reuptake inhibitors through alteration of the piperazine ring of 1-[2-(diphenylmethoxy)ethyl]- and 1-[2-[Bis(4-fluorophenyl)-methoxy]ethyl]-4-(3-phenylpropyl)piperazines (GBR 12935 and GBR 12909)
    • Matecka, D.; Rothman, R. B.; Radesca, L.; De Costa, B.; Dersch, C. M.; Partilla, J. S.; Pert, A.; Glowa, J. R.; Wojnicki, F. H.; Rice, K. C. Development of novel, potent, and selective dopamine reuptake inhibitors through alteration of the piperazine ring of 1-[2-(diphenylmethoxy)ethyl]- and 1-[2-[Bis(4-fluorophenyl)-methoxy]ethyl]-4-(3-phenylpropyl)piperazines (GBR 12935 and GBR 12909). J. Med. Chem. 1996, 39, 4704-4716.
    • (1996) J. Med. Chem. , vol.39 , pp. 4704-4716
    • Matecka, D.1    Rothman, R.B.2    Radesca, L.3    De Costa, B.4    Dersch, C.M.5    Partilla, J.S.6    Pert, A.7    Glowa, J.R.8    Wojnicki, F.H.9    Rice, K.C.10
  • 15
    • 0000254333 scopus 로고
    • Positional importance of the nitrogen atom in novel piperidine analogues of GBR 12909: Affinity and selectivity for the dopamine transporter
    • Dutta, A. K.; Meltzer, P. C.; Madras, B. K. Positional importance of the nitrogen atom in novel piperidine analogues of GBR 12909: Affinity and selectivity for the dopamine transporter. Med. Chem. Res. 1993, 3, 209-222.
    • (1993) Med. Chem. Res. , vol.3 , pp. 209-222
    • Dutta, A.K.1    Meltzer, P.C.2    Madras, B.K.3
  • 16
    • 0030043953 scopus 로고    scopus 로고
    • Structure-Activity Relationship Studies of Novel 4-[2-[Bis(4-fluorophenyl)methoxy]-ethyl]-1-(3-phenylpropyl)piperidine Analogues: Synthesis and Biological Evaluation at the Dopamine and Serotonin Transporter Sites
    • Dutta, A. K.; Xu, C.; Reith, M. E. A. Structure-Activity Relationship Studies of Novel 4-[2-[Bis(4-fluorophenyl)methoxy]-ethyl]-1-(3-phenylpropyl)piperidine Analogues: Synthesis and Biological Evaluation at the Dopamine and Serotonin Transporter Sites. J. Med. Chem. 1996, 39, 749-756.
    • (1996) J. Med. Chem. , vol.39 , pp. 749-756
    • Dutta, A.K.1    Xu, C.2    Reith, M.E.A.3
  • 17
    • 0031021652 scopus 로고    scopus 로고
    • Highly selective, novel analogues of 4-[2-(diphenylmethoxy)ethyl]-1-benzylpiperidine for the dopamine transporter: Effect of different aromatic substitutions on their affinity and selectivity
    • Dutta, A. K.; Coffey, L. L.; Reith, M. E. A. Highly selective, novel analogues of 4-[2-(diphenylmethoxy)ethyl]-1-benzylpiperidine for the dopamine transporter: Effect of different aromatic substitutions on their affinity and selectivity. J. Med. Chem. 1997, 40, 35-43.
    • (1997) J. Med. Chem. , vol.40 , pp. 35-43
    • Dutta, A.K.1    Coffey, L.L.2    Reith, M.E.A.3
  • 18
    • 0032567986 scopus 로고    scopus 로고
    • Potent and selective ligands for the dopamine transporter (DAT): Structure-activity relationship studies of novel 4-[2-(diphenylmethoxy)ethyl]-1-(3-phenylpropyl)piperidine analogues
    • Dutta, A. K.; Coffey, L. L.; Reith, M. E. A. Potent and selective ligands for the dopamine transporter (DAT): Structure-activity relationship studies of novel 4-[2-(diphenylmethoxy)ethyl]-1-(3-phenylpropyl)piperidine analogues. J. Med. Chem. 1998, 41, 699-705.
    • (1998) J. Med. Chem. , vol.41 , pp. 699-705
    • Dutta, A.K.1    Coffey, L.L.2    Reith, M.E.A.3
  • 19
    • 0026642039 scopus 로고
    • Probes for the cocaine receptor: Potentially irreversible ligands for the dopamine transporter
    • Carroll, F. I.; Gao, Y.; Abraham, P.; Lewin, A. H.; Lew, R.; Patel, A.; Boja, J. W.; Kuhar, M. J. Probes for the cocaine receptor: potentially irreversible ligands for the dopamine transporter. J. Med. Chem. 1992, 35, 1813-1817.
    • (1992) J. Med. Chem. , vol.35 , pp. 1813-1817
    • Carroll, F.I.1    Gao, Y.2    Abraham, P.3    Lewin, A.H.4    Lew, R.5    Patel, A.6    Boja, J.W.7    Kuhar, M.J.8
  • 23
    • 0029120376 scopus 로고
    • Effects of dopamine reuptake inhibitors on food- and cocaine-maintained responding: II. Comparisons with other drugs and repeated administrations
    • Glowa, J. R.; Wojnicki, F. H. E.; Matecka, D.; Rice, K. C.; Rothman, R. B. Effects of dopamine reuptake inhibitors on food- and cocaine-maintained responding: II. Comparisons with other drugs and repeated administrations. Exp. Clin. Psychopharmacol. 1995, 3, 232-239.
    • (1995) Exp. Clin. Psychopharmacol. , vol.3 , pp. 232-239
    • Glowa, J.R.1    Wojnicki, F.H.E.2    Matecka, D.3    Rice, K.C.4    Rothman, R.B.5
  • 25
    • 0001271559 scopus 로고
    • Carbodiimide-mediated amide formation in a two-phase system. a high-yield and low-racemization procedure for peptide synthesis
    • Ho, G.-J.; Emerson, K. M.; Mathre, D. J.; Shuman, R. F.; Grabowski, E. J. Carbodiimide-mediated amide formation in a two-phase system. A high-yield and low-racemization procedure for peptide synthesis. J. Org. Chem. 1995, 60, 3569-3570.
    • (1995) J. Org. Chem. , vol.60 , pp. 3569-3570
    • Ho, G.-J.1    Emerson, K.M.2    Mathre, D.J.3    Shuman, R.F.4    Grabowski, E.J.5
  • 26
    • 0029064866 scopus 로고
    • Characterization of a recombinant human dopamine transporter in multiple cell lines
    • Eshleman, A. J.; Neve, R. L.; Janowsky, A.; Neve, K. A. Characterization of a recombinant human dopamine transporter in multiple cell lines. J. Pharmacol. Exp. Ther. 1995, 274, 276-283.
    • (1995) J. Pharmacol. Exp. Ther. , vol.274 , pp. 276-283
    • Eshleman, A.J.1    Neve, R.L.2    Janowsky, A.3    Neve, K.A.4
  • 27
    • 0030930379 scopus 로고    scopus 로고
    • Metabolism of catecholamine by catechol-O-methyltransferase in cells expressing recombinant catecholamine transporters
    • Eshleman, A. J.; Stewart, E.; Evenson, A. K.; Mason, J. N.; Blakely, R. D.; Janowsky, A.; Neve, K. A. Metabolism of catecholamine by catechol-O-methyltransferase in cells expressing recombinant catecholamine transporters. J. Neurochem. 1997, 69, 1459-1466.
    • (1997) J. Neurochem. , vol.69 , pp. 1459-1466
    • Eshleman, A.J.1    Stewart, E.2    Evenson, A.K.3    Mason, J.N.4    Blakely, R.D.5    Janowsky, A.6    Neve, K.A.7
  • 29
  • 30
    • 0030575913 scopus 로고    scopus 로고
    • Binding domains for blockers and substrates on the cloned human dopamine transporter studied by protection against N-ethylmaleimide-induced reduction of 2beta-carboxy-3beta-(4-fluorophenyl)[3H]tropane ([3H]-WIN 35,428) binding
    • Reith, M. E. A.; Xu, C.; Coffey, L. L. Binding domains for blockers and substrates on the cloned human dopamine transporter studied by protection against N-ethylmaleimide-induced reduction of 2beta-carboxy-3beta-(4-fluorophenyl)[3H]tropane ([3H]-WIN 35,428) binding. Biochem. Pharmacol. 1996, 52, 1435-1446.
    • (1996) Biochem. Pharmacol. , vol.52 , pp. 1435-1446
    • Reith, M.E.A.1    Xu, C.2    Coffey, L.L.3
  • 31
    • 0028797473 scopus 로고
    • Translocation of dopamine and binding of 2 beta-carbomethoxy-3 beta-(4-fluorophenyl) tropane (Win 35,428) measured under identical conditions in rat striatal synaptosomal preparations. Inhibition by various blockers
    • Xu, C.; Coffey, L. L.; Reith, M. E. A. Translocation of dopamine and binding of 2 beta-carbomethoxy-3 beta-(4-fluorophenyl) tropane (WIN 35,428) measured under identical conditions in rat striatal synaptosomal preparations. Inhibition by various blockers. Biochem. Pharmacol. 1995, 49, 339-350.
    • (1995) Biochem. Pharmacol. , vol.49 , pp. 339-350
    • Xu, C.1    Coffey, L.L.2    Reith, M.E.A.3


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