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Volumn 18, Issue 4, 1999, Pages 342-353

Quantitative structure-activity relationships of phenyltropanes as inhibitors of three monoamine transporters: Classical and CoMFA studies

Author keywords

2D QSAR; CoMFA; Free Wilson analysis; Monoamine transporter; Phenyltropanes; PLS

Indexed keywords

COMPUTATIONAL CHEMISTRY; ION EXCHANGE; QUANTUM THEORY; SODIUM; STATISTICAL METHODS;

EID: 0032701926     PISSN: 09318771     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1521-3838(199910)18:4<342::AID-QSAR342>3.0.CO;2-E     Document Type: Article
Times cited : (22)

References (65)
  • 1
    • 0017043454 scopus 로고
    • Molecular geometry of inhibitors of the uptake of catecholamines and serotonin in synaptosomal preparations of rat brain
    • Koe, B.A., Molecular Geometry of Inhibitors of the Uptake of Catecholamines and Serotonin in Synaptosomal Preparations of Rat Brain, J. Pharmacol. Exp. Ther. 199, 649-661 (1976).
    • (1976) J. Pharmacol. Exp. Ther. , vol.199 , pp. 649-661
    • Koe, B.A.1
  • 2
    • 0022481325 scopus 로고
    • Structural requirements for cocaine congeners to interact with dopamine and serotonin uptake sites in mouse brain and to induce stereotyped behavior
    • Reith, M.E.A., Meisler, B.E., Sershen, H., and Lajtha, A., Structural Requirements for Cocaine Congeners to Interact with Dopamine and Serotonin Uptake Sites in Mouse Brain and to Induce Stereotyped Behavior, Biochem. Pharmacol. 35, 1123-1129 (1986).
    • (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, norepinephrine and serotonin transporters: A structure-activity study
    • Ritz, M.C., Cone, E.J., and Kuhar, M.J., Cocaine Inhibition of Ligand Binding at Dopamine, Norepinephrine and Serotonin Transporters: A Structure-Activity Study, Life Sci. 46, 635-645 (1990).
    • (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-administration of cocaine
    • Ritz, M.C., Lamb, R.J., Goldberg, R., and Kuhar, M.J., Cocaine Receptors on Dopamine Transporters are Related to Self-Administration of Cocaine, Science 237, 1219-1223 (1987).
    • (1987) Science , vol.237 , pp. 1219-1223
    • Ritz, M.C.1    Lamb, R.J.2    Goldberg, R.3    Kuhar, M.J.4
  • 5
    • 0024460030 scopus 로고
    • Effects of cocaine and related drugs in nonhuman primates. III. Self-administration by Squirrel Monkeys
    • Bergman, J., Madras, B.K., Johnson, S.E., and Spealman, R.D., Effects of Cocaine and Related Drugs in Nonhuman Primates. III. Self-Administration by Squirrel Monkeys, J. Pharmacol. Exp. Ther. 251, 150-155 (1989).
    • (1989) J. Pharmacol. Exp. Ther. , vol.251 , pp. 150-155
    • Bergman, J.1    Madras, B.K.2    Johnson, S.E.3    Spealman, R.D.4
  • 6
    • 0025924705 scopus 로고
    • 2 mediation of the discriminative stimulus properties of d-Amphetamine and cocaine
    • 2 Mediation of the Discriminative Stimulus Properties of d-Amphetamine and Cocaine, Psychopharmacology 103, 50-55 (1991).
    • (1991) Psychopharmacology , vol.103 , pp. 50-55
    • Callahan, P.M.1    Appel, J.B.2    Cunningham, K.A.3
  • 8
    • 0024456087 scopus 로고
    • Effects of cocaine and related drugs in nonhuman primates. II. Stimulant effects on schedule-controlled behavior
    • Spealman, R.D., Madras, B.K., and Bergman, J., Effects of Cocaine and Related Drugs in Nonhuman Primates. II. Stimulant Effects on Schedule-Controlled Behavior, J. Pharmacol. Exp. Ther. 251, 142-149 (1989).
    • (1989) J. Pharmacol. Exp. Ther. , vol.251 , pp. 142-149
    • Spealman, R.D.1    Madras, B.K.2    Bergman, J.3
  • 9
    • 0001823451 scopus 로고
    • Cocaine: Discussion on the role of dopamine in the biochemical mechanism of action
    • Ellinwood, E.H., and Kilbey, M.M. (Eds.), Plenum Press, New York
    • Scheel-Krüger, J., Braestrup, C., Nielsen, M., Golembiowska, K., and Mogilnicka, E., Cocaine: Discussion on the Role of Dopamine in the Biochemical Mechanism of Action, in: Ellinwood, E.H., and Kilbey, M.M. (Eds.), Cocaine and other Stimulants, Plenum Press, New York 1976, pp. 373-407.
    • (1976) Cocaine and Other Stimulants , pp. 373-407
    • Scheel-Krüger, J.1    Braestrup, C.2    Nielsen, M.3    Golembiowska, K.4    Mogilnicka, E.5
  • 10
    • 0018570011 scopus 로고
    • Motor activity and rotational behavior after analogs of cocaine: Correlation with dopamine uptake blockade
    • Heikkila, R.E., Cabbat, F.S., and Duvoisin, R.C., Motor Activity and Rotational Behavior after Analogs of Cocaine: Correlation with Dopamine Uptake Blockade, Commun. Psychopharmacol. 3, 285-290 (1979).
    • (1979) Commun. Psychopharmacol. , vol.3 , pp. 285-290
    • Heikkila, R.E.1    Cabbat, F.S.2    Duvoisin, R.C.3
  • 11
    • 0018637994 scopus 로고
    • Rotational behavior induced by cocaine analogs in rats with unilateral 6-hydroxydopamine lesions of the substantia nigra: Dependence upon dopamine uptake inhibition
    • Heikkila, R.E., Cabbat, F.S., Manzino, L., and Duvoisin, R.C., Rotational Behavior Induced by Cocaine Analogs in Rats with Unilateral 6-hydroxydopamine Lesions of the Substantia Nigra: Dependence upon Dopamine Uptake Inhibition, J. Pharmacol. Exp. Ther. 211, 189-194 (1979).
    • (1979) J. Pharmacol. Exp. Ther. , vol.211 , pp. 189-194
    • Heikkila, R.E.1    Cabbat, F.S.2    Manzino, L.3    Duvoisin, R.C.4
  • 12
    • 0031037946 scopus 로고    scopus 로고
    • Serotonergic mechanism involved in the discriminative stimulus, reinforcing and subjective effects of cocaine
    • Walsh, S.L., and Cunningham, K.A., Serotonergic Mechanism Involved in the Discriminative Stimulus, Reinforcing and Subjective Effects of Cocaine, Psychopharmacology 130, 41-58 (1997).
    • (1997) Psychopharmacology , vol.130 , pp. 41-58
    • Walsh, S.L.1    Cunningham, K.A.2
  • 13
    • 0027257999 scopus 로고
    • Modification of behavioral effects of cocaine by selective serotonin and dopamine uptake inhibitors in Squirrel Monkeys
    • Spealman, R.D., Modification of Behavioral Effects of Cocaine by Selective Serotonin and Dopamine Uptake Inhibitors in Squirrel Monkeys, Psychopharmacology 112, 93-99 (1993).
    • (1993) Psychopharmacology , vol.112 , pp. 93-99
    • Spealman, R.D.1
  • 14
    • 0029549859 scopus 로고
    • Serotonergic modulation of the behavioral effects of cocaine in the Squirrel Monkey
    • Howell, L.L., and Byrd, L.D., Serotonergic Modulation of the Behavioral Effects of Cocaine in the Squirrel Monkey, J. Pharmacol. Exp. Ther. 275, 1551-1559 (1995).
    • (1995) J. Pharmacol. Exp. Ther. , vol.275 , pp. 1551-1559
    • Howell, L.L.1    Byrd, L.D.2
  • 15
    • 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., and 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. 36, 2886-2890 (1993).
    • (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
  • 16
    • 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., and 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. 38, 379-388 (1995).
    • (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
  • 17
    • 0029796134 scopus 로고    scopus 로고
    • Synthesis and transporter binding properties of 3β-(4′-alkyl-, 4′-alkenyl-, and 4′-alkynylphenyl)nortropane-2β-carboxylic acid methyl esters: Serotonin transporter selective analogs
    • Blough, B.E., Abraham, P., Lewin, A.H., Kuhar, M.J., Boja, J.W., and Carroll, F.I., Synthesis and Transporter Binding Properties of 3β-(4′-Alkyl-, 4′-alkenyl-, and 4′-alkynylphenyl)nortropane-2β-carboxylic Acid Methyl Esters: Serotonin Transporter Selective Analogs, J. Med. Chem. 39, 4027-4035 (1996).
    • (1996) J. Med. Chem. , vol.39 , pp. 4027-4035
    • Blough, B.E.1    Abraham, P.2    Lewin, A.H.3    Kuhar, M.J.4    Boja, J.W.5    Carroll, F.I.6
  • 19
    • 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., and 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. 35, 4764-4766 (1992).
    • (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
  • 20
    • 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., and Carroll, F.I., 2β-Substituted Analogues of Cocaine. Synthesis and Inhibition of Binding to the Cocaine Receptor, J. Med. Chem. 35, 135-140 (1992).
    • (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
  • 21
    • 0026584581 scopus 로고
    • N-modified analogues of cocaine: Synthesis and inhibition of binding to the cocaine receptor
    • Abraham, P., Pitter, J.B., Lewin, A.H., Boja, J.W., Kuhar, M.J., and Carroll, F.I., N-Modified Analogues of Cocaine: Synthesis and Inhibition of Binding to the Cocaine Receptor, J. Med. Chem. 35, 141-144 (1992).
    • (1992) J. Med. Chem. , vol.35 , pp. 141-144
    • Abraham, P.1    Pitter, J.B.2    Lewin, A.H.3    Boja, J.W.4    Kuhar, M.J.5    Carroll, F.I.6
  • 22
    • 0028062672 scopus 로고
    • Structure-activity relationship studies of N-sulfonyl analogs of cocaine: Role of ionic interactions in cocaine binding
    • Kozikowski, A.P., Eddine Saiah, M.K., Bergmann, J.S., and Johnson, K.M., Structure-Activity Relationship Studies of N-Sulfonyl Analogs of Cocaine: Role of Ionic Interactions in Cocaine Binding, J. Med. Chem. 37, 3440-3442 (1994).
    • (1994) J. Med. Chem. , vol.37 , pp. 3440-3442
    • Kozikowski, A.P.1    Eddine Saiah, M.K.2    Bergmann, J.S.3    Johnson, K.M.4
  • 24
    • 0030788357 scopus 로고    scopus 로고
    • Synthesis and ligand binding studies of 4′-iodobenzoyl esters of tropanes and piperidines at the dopamine transporter
    • Singh, S., Basmadjian, G.P., Avor, K.S., Pouw, B., Seale, T.W., Synthesis and Ligand Binding Studies of 4′-Iodobenzoyl Esters of Tropanes and Piperidines at the Dopamine Transporter, J. Med. Chem. 40, 2474-2481 (1997).
    • (1997) J. Med. Chem. , vol.40 , pp. 2474-2481
    • Singh, S.1    Basmadjian, G.P.2    Avor, K.S.3    Pouw, B.4    Seale, T.W.5
  • 25
    • 0032543297 scopus 로고    scopus 로고
    • 2β-Substituted analogues of 4′-iodococaine: Synthesis and dopamine transporter binding potencies
    • Avor, K.S., Singh, S., Seale, T.W., Pouw, B., and Basmadjian, G.P., 2β-Substituted Analogues of 4′-Iodococaine: Synthesis and Dopamine Transporter Binding Potencies, J. Med. Chem. 41, 2380-2389 (1998).
    • (1998) J. Med. Chem. , vol.41 , pp. 2380-2389
    • Avor, K.S.1    Singh, S.2    Seale, T.W.3    Pouw, B.4    Basmadjian, G.P.5
  • 26
    • 0001388194 scopus 로고
    • Use of Nitrile Oxide Cycloaddition (NOC) chemistry in the synthesis of cocaine analogues, mazindol binding and dopamine uptake studies
    • Kozikowski, A.P., Xiang, L., Tanaka, J., Bergmann, J.S., and Johnson, K.M., Use of Nitrile Oxide Cycloaddition (NOC) Chemistry in the Synthesis of Cocaine Analogues, Mazindol Binding and Dopamine Uptake Studies, Med. Chem. Res. 1, 312-321 (1991).
    • (1991) Med. Chem. Res. , vol.1 , pp. 312-321
    • Kozikowski, A.P.1    Xiang, L.2    Tanaka, J.3    Bergmann, J.S.4    Johnson, K.M.5
  • 27
    • 0026073889 scopus 로고
    • Synthesis of 3-carbamoylecgonine methyl ester analogues as inhibitors of cocaine binding and dopamine uptake
    • Kline, R.H., Wright, J., Eshleman, A.J., Fox, K.M., and Eldefrawi, M.D., Synthesis of 3-Carbamoylecgonine Methyl Ester Analogues as Inhibitors of Cocaine Binding and Dopamine Uptake, J. Med. Chem. 34, 702-705 (1991).
    • (1991) J. Med. Chem. , vol.34 , pp. 702-705
    • Kline, R.H.1    Wright, J.2    Eshleman, A.J.3    Fox, K.M.4    Eldefrawi, M.D.5
  • 28
    • 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., Clifford, G., and Madras, B.K., 2-Carbomethoxy-3-aryl-8-oxabicyclo[3.2.1]octanes: Potent Non-Nitrogen Inhibitors of Monoamine Transporters, J. Med. Chem. 40, 2661-2673 (1997).
    • (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    Clifford, G.6    Madras, B.K.7
  • 29
    • 0026009418 scopus 로고
    • Synthesis, ligand binding, QSAR and CoMFA study of 3β-(p-substituted phenyl)tropane-2β-carboxylic acid methyl esters
    • Carroll, F.I., Gao, Y., Rahman, M.A., Abraham, P., Parham, K., Lewin, A.H., and Boja, J.W., Synthesis, Ligand Binding, QSAR and CoMFA Study of 3β-(p-Substituted phenyl)tropane-2β-carboxylic Acid Methyl Esters, J. Med. Chem. 34, 2719-2725 (1991).
    • (1991) J. Med. Chem. , vol.34 , pp. 2719-2725
    • Carroll, F.I.1    Gao, Y.2    Rahman, M.A.3    Abraham, P.4    Parham, K.5    Lewin, A.H.6    Boja, J.W.7
  • 30
    • 0027968806 scopus 로고
    • Synthesis, ligand binding, and QSAR (CoMFA and classical) study of 3β-(3′-substituted phenyl)-, 3β-(4′-substituted phenyl)-, and 3β-(3′,4′-disubstituted phenyl)tropane-2β-carboxylic acid methyl esters
    • Carroll, F.I., Mascarella, S.W., Kuzemko, M.A., Gao, Y., Abraham, P., Lewin, A.M., Boja, J.W., and Kuhar, M.J., Synthesis, Ligand Binding, and QSAR (CoMFA and classical) Study of 3β-(3′-Substituted phenyl)-, 3β-(4′-Substituted phenyl)-, and 3β-(3′,4′-Disubstituted phenyl)tropane-2β-carboxylic Acid Methyl Esters, J. Med. Chem. 37, 2865-2873 (1994).
    • (1994) J. Med. Chem. , vol.37 , pp. 2865-2873
    • Carroll, F.I.1    Mascarella, S.W.2    Kuzemko, M.A.3    Gao, Y.4    Abraham, P.5    Lewin, A.M.6    Boja, J.W.7    Kuhar, M.J.8
  • 31
    • 0027131603 scopus 로고
    • Analysis of cocaine receptor site ligand binding by three-dimension voronoi site modeling approach
    • Srivastava, S., Crippen, G.M., Analysis of Cocaine Receptor Site Ligand Binding by Three-Dimension Voronoi Site Modeling Approach, J. Med. Chem. 36, 3572-3579 (1993).
    • (1993) J. Med. Chem. , vol.36 , pp. 3572-3579
    • Srivastava, S.1    Crippen, G.M.2
  • 32
    • 0030449505 scopus 로고    scopus 로고
    • Synthesis and dopamine transporter affinity of 2-(methoxycarbonyl)-9-methyl-3-phenyl-9-azabicyclo [3.3.1]nonane derivatives
    • Chen, Z., Izenwasser, S., Katz, J.L., Zhu, N., Klein, C.L., and Trudell, M.L., Synthesis and Dopamine Transporter Affinity of 2-(Methoxycarbonyl)-9-methyl-3-phenyl-9-azabicyclo [3.3.1]nonane Derivatives, J. Med. Chem. 39, 4744-4749 (1996).
    • (1996) J. Med. Chem. , vol.39 , pp. 4744-4749
    • Chen, Z.1    Izenwasser, S.2    Katz, J.L.3    Zhu, N.4    Klein, C.L.5    Trudell, M.L.6
  • 33
    • 14444270841 scopus 로고    scopus 로고
    • Synthesis and ligand binding of nortropane derivatives: N-substituted 2β-carbomethoxy-3β-(4′-iodophenyl)nortropane and N-(3-iodoprop-(2E)-enyl)-2β-carbomethoxy-3β-(3′,4′- disubstituted phenyl)nortropane. New high-affinity and selective compounds for the dopamine transporter
    • Emond, P., Garreau, L., Chalon, S., Boazi, M., Caillet, M., Bricard, J., Frangin, Y., Mauclaire, L., Besnard, J.C., and Guilloteau, D., Synthesis and Ligand Binding of Nortropane Derivatives: N-Substituted 2β-Carbomethoxy-3β-(4′-iodophenyl)nortropane and N-(3-Iodoprop-(2E)-enyl)-2β-carbomethoxy-3β-(3′,4′- disubstituted phenyl)nortropane. New High-Affinity and Selective Compounds for the Dopamine Transporter, J. Med. Chem. 40, 1366-1372 (1997).
    • (1997) J. Med. Chem. , vol.40 , pp. 1366-1372
    • Emond, P.1    Garreau, L.2    Chalon, S.3    Boazi, M.4    Caillet, M.5    Bricard, J.6    Frangin, Y.7    Mauclaire, L.8    Besnard, J.C.9    Guilloteau, D.10
  • 34
    • 0030070681 scopus 로고    scopus 로고
    • N-substituted analogs of 2β-carbomethoxy-3β-(4′-iodophenyl)tropane (β-CIT) with selective affinity to dopamine or serotonin transporters in rat forebrain
    • Neumeyer, J.L., Tamagnan, G., Wang, S., Gao, Y., Milius, R.A., Kula, N.S., and Baldessarini, R.J., N-Substituted Analogs of 2β-Carbomethoxy-3β-(4′-iodophenyl)tropane (β-CIT) with Selective Affinity to Dopamine or Serotonin Transporters in Rat Forebrain, J. Med. Chem. 39, 543-548 (1996).
    • (1996) J. Med. Chem. , vol.39 , pp. 543-548
    • Neumeyer, J.L.1    Tamagnan, G.2    Wang, S.3    Gao, Y.4    Milius, R.A.5    Kula, N.S.6    Baldessarini, R.J.7
  • 35
    • 0028773367 scopus 로고
    • Secondary amine analogues of 2β-(4′-sustituted phenyl)tropane-2β-carboxylic acid esters and N-norcocaine exhibit enhanced affinity for serotonin and norepinephrine transporters
    • Boja, J.W., Kuhar, M.J., Kopajtic, T., Yang, E., Abraham, P., Lewin, A.H., and Carroll, F.I., Secondary Amine Analogues of 2β-(4′-Sustituted phenyl)tropane-2β-carboxylic Acid Esters and N-Norcocaine Exhibit Enhanced Affinity for Serotonin and Norepinephrine Transporters, J. Med. Chem. 37, 1220-1223 (1994).
    • (1994) J. Med. Chem. , vol.37 , pp. 1220-1223
    • Boja, J.W.1    Kuhar, M.J.2    Kopajtic, T.3    Yang, E.4    Abraham, P.5    Lewin, A.H.6    Carroll, F.I.7
  • 36
    • 0025895074 scopus 로고
    • Synthesis and receptor binding of N-substituted tropane derivatives. High-affinity ligands for the cocaine receptor
    • Milius, R.A., Saha, J.K., Madras, B.K., Neumeyer, J.L., Synthesis and Receptor Binding of N-Substituted Tropane Derivatives. High-Affinity Ligands for the Cocaine Receptor, J. Med. Chem. 34, 1728-1731 (1991).
    • (1991) J. Med. Chem. , vol.34 , pp. 1728-1731
    • Milius, R.A.1    Saha, J.K.2    Madras, B.K.3    Neumeyer, J.L.4
  • 37
    • 0030896771 scopus 로고    scopus 로고
    • Synthesis, dopamine transporter affinity, dopamine uptake inhibition, and locomotor stimulant activity of 2-substituted 3β-phenyltropane derivatives
    • Xu, L., Kelkar, S.V., Lomenzo, S.A., Izenwasser, S., Katz, J.L., Kline, R.H., and Trudell, M.L., Synthesis, Dopamine Transporter Affinity, Dopamine Uptake Inhibition, and Locomotor Stimulant Activity of 2-Substituted 3β-Phenyltropane Derivatives, J. Med. Chem. 40, 858-863 (1997).
    • (1997) J. Med. Chem. , vol.40 , pp. 858-863
    • Xu, L.1    Kelkar, S.V.2    Lomenzo, S.A.3    Izenwasser, S.4    Katz, J.L.5    Kline, R.H.6    Trudell, M.L.7
  • 38
    • 0027987234 scopus 로고
    • Synthesis, cocaine receptor affinity, and dopamine uptake inhibition of several new 2β-substituted 3β-phenyltropanes
    • Kelkar, S.V., Izenwasser, S., Katz, J.L., Klein, C.L., Zhu, N., and Trudell, M.L., Synthesis, Cocaine Receptor Affinity, and Dopamine Uptake Inhibition of Several New 2β-Substituted 3β-Phenyltropanes, J. Med. Chem. 37, 3875-3877 (1994).
    • (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
  • 39
    • 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., and Kuhar, M.J., Probes for the Cocaine Receptor. Potentially Irreversible Ligands for the Dopamine Transporter, J. Med. Chem. 35, 1813-1817 (1992).
    • (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
  • 40
    • 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., Ball, 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. 3, 1327-1332 (1993).
    • (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    Ball, R.G.5
  • 41
    • 0030729033 scopus 로고    scopus 로고
    • 3β-(4-ethyl-3-iodophenyl)nortropane-2β-carboxylic acid methyl ester as a high-affinity selective ligand for the serotonin transporter
    • Blough, B.E., Abraham, P., Mills, A.C., Lewin, A.H., Boja, J.W., Scheffel, U., Kuhar, M.J., and Carroll, F.I., 3β-(4-Ethyl-3-iodophenyl)nortropane-2β-carboxylic Acid Methyl Ester as a High-Affinity Selective Ligand for the Serotonin Transporter, J. Med. Chem. 40, 3861-3864 (1997).
    • (1997) J. Med. Chem. , vol.40 , pp. 3861-3864
    • Blough, B.E.1    Abraham, P.2    Mills, A.C.3    Lewin, A.H.4    Boja, J.W.5    Scheffel, U.6    Kuhar, M.J.7    Carroll, F.I.8
  • 42
    • 0029992705 scopus 로고    scopus 로고
    • Synthesis of 3β-aryl-8-azabicyclo[3.2.1]octanes with high binding affinities and selectivities for the serotonin transporter site
    • Davies, H.M.L., Kuhn, L.A., Thornley, C., Matasi, J.J., Sexton, T., and Childers, S.R., Synthesis of 3β-Aryl-8-azabicyclo[3.2.1]octanes with High Binding Affinities and Selectivities for the Serotonin Transporter Site, J. Med. Chem. 39, 2554-2558 (1996).
    • (1996) J. Med. Chem. , vol.39 , pp. 2554-2558
    • Davies, H.M.L.1    Kuhn, L.A.2    Thornley, C.3    Matasi, J.J.4    Sexton, T.5    Childers, S.R.6
  • 43
    • 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., and 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. 37, 1262-1268 (1994).
    • (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
  • 44
    • 0027468956 scopus 로고
    • Substituted 3-phenyltropane analogs of cocaine: Synthesis, inhibition of binding at cocaine recognition sites, and positron emission tomography imaging
    • Meltzer, P.C., Liang, A.Y., Brownell, A.L., Elmaleh, D.R., Madras, B.K., Substituted 3-Phenyltropane Analogs of Cocaine: Synthesis, Inhibition of Binding at Cocaine Recognition Sites, and Positron Emission Tomography Imaging, J. Med. Chem. 36, 855-862 (1993).
    • (1993) J. Med. Chem. , vol.36 , pp. 855-862
    • Meltzer, P.C.1    Liang, A.Y.2    Brownell, A.L.3    Elmaleh, D.R.4    Madras, B.K.5
  • 45
    • 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., Mascarella, W., Abraham, P., Lewin, A.H., Boja, J.W., Kuhar, M.J., and 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. 39, 2753-2763 (1996).
    • (1996) J. Med. Chem. , vol.39 , pp. 2753-2763
    • Kotian, P.1    Mascarella, W.2    Abraham, P.3    Lewin, A.H.4    Boja, J.W.5    Kuhar, M.J.6    Carroll, F.I.7
  • 46
    • 0029824217 scopus 로고    scopus 로고
    • 3α-(4′-substituted phenyl)tropane-2β-carboxylic acid methyl esters: Novel ligands with high affinity and selectivity at the dopamine transporter
    • Holmquist, C.R., Keverline-Frantz, K.I., Abraham, P., Boja, J.W., Kuhar, M.J., and Carroll, F.I., 3α-(4′-Substituted phenyl)tropane-2β-carboxylic Acid Methyl Esters: Novel Ligands with High Affinity and Selectivity at the Dopamine Transporter, J. Med. Chem. 39, 4139-4141 (1996).
    • (1996) J. Med. Chem. , vol.39 , pp. 4139-4141
    • Holmquist, C.R.1    Keverline-Frantz, K.I.2    Abraham, P.3    Boja, J.W.4    Kuhar, M.J.5    Carroll, F.I.6
  • 47
    • 0028903389 scopus 로고
    • Novel 2-substituted cocaine analogs: Uptake and ligand binding studies at dopamine, serotonin and norepinephrine transport sites in the rat brain
    • Bennett, B.A., Wichems, C.H., Hollingsworth, C.K., Davies, H.M.L., Thornley, C., Sexton, T., Childers, S.R., Novel 2-Substituted Cocaine Analogs: Uptake and Ligand Binding Studies at Dopamine, Serotonin and Norepinephrine Transport Sites in the Rat Brain, J. Pharmacol. Exp. Ther. 272,1176-1186 (1995).
    • (1995) J. Pharmacol. Exp. Ther. , vol.272 , pp. 1176-1186
    • Bennett, B.A.1    Wichems, C.H.2    Hollingsworth, C.K.3    Davies, H.M.L.4    Thornley, C.5    Sexton, T.6    Childers, S.R.7
  • 49
    • 0029122828 scopus 로고
    • Chemistry and biology of the 2β-alkyl-3β-phenyl analogues of cocaine: Subnanomolar affinity ligands that suggest a new pharmacophore model at the C-2 position
    • Kozikowski, A.P., Eddine Saiah, M.K., Johnson, K.M., Bergmann, J.S., Chemistry and Biology of the 2β-Alkyl-3β-phenyl Analogues of Cocaine: Subnanomolar Affinity Ligands That Suggest a New Pharmacophore Model at the C-2 Position, J. Med. Chem. 38, 3086-3093 (1995).
    • (1995) J. Med. Chem. , vol.38 , pp. 3086-3093
    • Kozikowski, A.P.1    Eddine Saiah, M.K.2    Johnson, K.M.3    Bergmann, J.S.4
  • 50
    • 0032543634 scopus 로고    scopus 로고
    • Synthesis and dopamine transporter affinity of the four stereoisomers of (±)-2-(methoxycarbonyl)-7-methyl-3-phenyl-7-azabicyclo[2.2.1]heptane
    • Zhang, C., Izenwasser, S., Katz, J.L., Terry, P.D., Trudell, M.L., Synthesis and Dopamine Transporter Affinity of the Four Stereoisomers of (±)-2-(Methoxycarbonyl)-7-methyl-3-phenyl-7-azabicyclo[2.2.1]heptane, J. Med. Chem. 41, 2430-2435 (1998).
    • (1998) J. Med. Chem. , vol.41 , pp. 2430-2435
    • Zhang, C.1    Izenwasser, S.2    Katz, J.L.3    Terry, P.D.4    Trudell, M.L.5
  • 51
    • 0031450277 scopus 로고    scopus 로고
    • Synthesis, structure, dopamine transporter affinity, and dopamine uptake inhibition of 6-alkyl-3-benzyl-2-[(methoxycarbonyl)-methyl]tropane derivatives
    • Lomenzo, S.A., Izenwasser, S., Katz, J.L., Terry, P.D., Zhu, N., Klein, C.L., and Trudell, M.L., Synthesis, Structure, Dopamine Transporter Affinity, and Dopamine Uptake Inhibition of 6-Alkyl-3-benzyl-2-[(methoxycarbonyl)-methyl]tropane Derivatives, J. Med. Chem. 40, 4406-4414 (1997).
    • (1997) J. Med. Chem. , vol.40 , pp. 4406-4414
    • Lomenzo, S.A.1    Izenwasser, S.2    Katz, J.L.3    Terry, P.D.4    Zhu, N.5    Klein, C.L.6    Trudell, M.L.7
  • 53
    • 85192677246 scopus 로고    scopus 로고
    • CAMO ASA, Olav Tryggvasonsgt. 24, N-7011 Trondheim, Norway
    • CAMO ASA, Olav Tryggvasonsgt. 24, N-7011 Trondheim, Norway.
  • 54
    • 85192670028 scopus 로고    scopus 로고
    • Umetri AB, Box 7960, S-907 19 Umeå, Sweden
    • Umetri AB, Box 7960, S-907 19 Umeå, Sweden.
  • 55
    • 85192677671 scopus 로고    scopus 로고
    • Tripos Inc., 1699 Hanley Road, St. Louis, MO 63144-2913, USA
    • Tripos Inc., 1699 Hanley Road, St. Louis, MO 63144-2913, USA.
  • 57
    • 85192674141 scopus 로고    scopus 로고
    • Oxford Molecular LTD., The Medawar Centre, Oxford Science Park, Oxford OX4 4 GA, UK
    • Oxford Molecular LTD., The Medawar Centre, Oxford Science Park, Oxford OX4 4 GA, UK.
  • 58
    • 85192675782 scopus 로고    scopus 로고
    • ftp.ipc.pku.edu.cn: /pub/software/aos_aps/
  • 59
    • 85192673612 scopus 로고    scopus 로고
    • BioByte Corp., 201 W. Fourth Street, Suite #204, Claremont, CA 91711-4707, USA
    • BioByte Corp., 201 W. Fourth Street, Suite #204, Claremont, CA 91711-4707, USA.
  • 61
    • 0003626523 scopus 로고    scopus 로고
    • Cambridge Crystallographic Data Centre, University Chemical Laboratory, Cambridge, UK
    • Cambridge Crystallographic Database, Cambridge Crystallographic Data Centre, University Chemical Laboratory, Cambridge, UK.
    • Cambridge Crystallographic Database
  • 63
    • 0004480112 scopus 로고    scopus 로고
    • A critical review of recent CoMFA applications
    • Kubinyi, H., Folkers, G., and Martin, Y.C. (Eds.), Kluwer/ESCOM, Dordrecht
    • Kim, K.I., Greco, G., and Novellino, E., A Critical Review of Recent CoMFA Applications, in: Kubinyi, H., Folkers, G., and Martin, Y.C. (Eds.), 3D QSAR in Drug Design: Recent Advances, Kluwer/ESCOM, Dordrecht 1998, pp. 257-315.
    • (1998) 3D QSAR in Drug Design: Recent Advances , pp. 257-315
    • Kim, K.I.1    Greco, G.2    Novellino, E.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.