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Volumn 47, Issue 21, 2004, Pages 5101-5113

Further structurally constrained analogues of cis-(6-benzhydrylpiperidin-3- yl)benzylamine with elucidation of bioactive conformation: Discovery of 1,4-diazabicyclo[3.3.1]nonane derivatives and evaluation of their biological properties for the monoamine transporters

Author keywords

[No Author keywords available]

Indexed keywords

3BETA (4 FLUOROPHENYL) 2BETA TROPANECARBOXYLIC ACID METHYL ESTER; 8 BENZHYDRYL 1,4 DIAZABICYCLO[3.3.1]NONANE; 8 BENZHYDRYL 4 (3,4 DICHLOROBENZYL) 1,4 DIAZABICYCLO[3.3.1]NONANE; 8 BENZHYDRYL 4 (4 ETHOXYBENZYL) 1,4 DIAZABICYCLO[3.3.1]NONANE; 8 BENZHYDRYL 4 (4 FLUOROBENZYL) 1,4 DIAZABICYCLO[3.3.1]NONANE; 8 BENZHYDRYL 4 (4 METHOXYBENZYL) 1,4 DIAZABICYCLO[3.3.1]NONANE; 8 BENZHYDRYL 4 (4 NITROBENZYL) 1,4 DIAZABICYCLO[3.3.1]NONANE; 8 BENZHYDRYL 4 [2 (4 FLUOROPHENYL)ETHYL] 1,4 DIAZABICYCLO[3.3.1]NONANE; 8 BENZHYDRYL 4 METHYL 1,4 DIAZABICYCLO[3.3.1]NONANE; 8 BENZHYDRYL 4 NAPHTHALEN 1 YLMETHYL 1,4 DIAZABICYCLO[3.3.1]NONANE; 8 BENZHYDRYL 4 NAPHTHALEN 2 YLMETHYL 1,4 DIAZABICYCLO[3.3.1]NONANE; BENZHYDRYL DERIVATIVE; CIS(6 BENZHYDRYLPIPERIDIN 3 YL)BENZYLAMINE; CITALOPRAM; DOPAMINE TRANSPORTER; NISOXETINE; NORADRENALIN TRANSPORTER; SEROTONIN TRANSPORTER; TRITIUM; UNCLASSIFIED DRUG;

EID: 4744375699     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm049796t     Document Type: Article
Times cited : (18)

References (35)
  • 1
    • 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
  • 2
    • 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
  • 3
    • 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
  • 4
    • 0025895413 scopus 로고
    • Behavioral effects of selective dopaminergic compounds in rats discriminating cocaine injections
    • Witkin, J. M.; Nichols, D. E.; Terry, P.; Katz, J. L. Behavioral effects of selective dopaminergic compounds in rats discriminating cocaine injections. J. Pharmacol. Exp. Ther. 1991, 257, 706-713.
    • (1991) J. Pharmacol. Exp. Ther. , vol.257 , pp. 706-713
    • Witkin, J.M.1    Nichols, D.E.2    Terry, P.3    Katz, J.L.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
    • 0024456087 scopus 로고
    • Effects of Cocaine and Related Drugs in Nonhuman Primates. II. Stimulant Effects on Schedule-Controlled
    • 1989.
    • Spealman, R. D.; Madras, B. K.; Bergman, J. 1989. Effects of Cocaine and Related Drugs in Nonhuman Primates. II. Stimulant Effects on Schedule-Controlled Behav. Pharmacol. Exp. Ther. 1989, 251, 142-149.
    • (1989) Behav. Pharmacol. Exp. Ther. , vol.251 , pp. 142-149
    • Spealman, R.D.1    Madras, B.K.2    Bergman, J.3
  • 7
    • 0035347177 scopus 로고    scopus 로고
    • Cocaine and Amphetamine Increase Extracellular Dopamine in the Nucleus Accumbens of Mice Lacking the Dopamine Transporter Gene
    • Carboni, E.; Spielewoy, C.; Vacca, C.; Nosten-Bertrand M.; Giros, B.; Di Chiara, G. Cocaine and Amphetamine Increase Extracellular Dopamine in the Nucleus Accumbens of Mice Lacking the Dopamine Transporter Gene. J. Neurosci. 2001, 21, RC141.
    • (2001) J. Neurosci. , vol.21
    • Carboni, E.1    Spielewoy, C.2    Vacca, C.3    Nosten-Bertrand, M.4    Giros, B.5    Di Chiara, G.6
  • 8
    • 0031037946 scopus 로고    scopus 로고
    • Serotonergic mechanisms involved in the discriminative stimulus, reinforcing and subjective effects of cocaine
    • Walsh, S. L.; Cunningham, K. A. Serotonergic mechanisms involved in the discriminative stimulus, reinforcing and subjective effects of cocaine. Psychopharmacology 1997, 130, 41-58.
    • (1997) Psychopharmacology , vol.130 , pp. 41-58
    • Walsh, S.L.1    Cunningham, K.A.2
  • 9
    • 0033615028 scopus 로고    scopus 로고
    • Pharmacotherapies for Treatment of Cocaine Abuse: Preclinical Aspects
    • Carroll, F. I.; Howell, L. L.; Kuhar, M. J. Pharmacotherapies for Treatment of Cocaine Abuse: Preclinical Aspects. J. Med. Chem. 1999, 42, 2721-2736.
    • (1999) J. Med. Chem. , vol.42 , pp. 2721-2736
    • Carroll, F.I.1    Howell, L.L.2    Kuhar, M.J.3
  • 10
  • 11
    • 0001384546 scopus 로고    scopus 로고
    • Chemistry, design, and structure-activity relationship of cocaine antagonists
    • Singh, S. Chemistry, design, and structure-activity relationship of cocaine antagonists. Chem. Rev. 2000, 100, 925-1024.
    • (2000) Chem. Rev. , vol.100 , pp. 925-1024
    • Singh, S.1
  • 12
    • 0242408732 scopus 로고    scopus 로고
    • Dopamine transporter as target for drug development of cocaine dependence medications
    • Dutta, A, K.; Zhang, S.; Kolhatkar, R.; Reith, M. E. A. Dopamine transporter as target for drug development of cocaine dependence medications. Eu. J. Pharmacol. 2003, 479, 93-106.
    • (2003) Eu. J. Pharmacol. , vol.479 , pp. 93-106
    • Dutta, A.K.1    Zhang, S.2    Kolhatkar, R.3    Reith, M.E.A.4
  • 13
    • 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
  • 14
    • 0031021652 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. 1897, 40, 35-43.
    • (1897) J. Med. Chem. , vol.40 , pp. 35-43
    • Dutta, A.K.1    Coffey, L.L.2    Reith, M.E.A.3
  • 15
    • 0035866586 scopus 로고    scopus 로고
    • Structure-Activity Relationship Studies of 4-[2-(Diphenylmethoxy)-ethyl]- 1-benzylpiperidine Derivatives and their N- Analogues: Evaluation of Behavioral Activity of O-and N-Analogues and their Binding to Monoamine transporters
    • Dutta, A. K.; Fei, X.-S.; Beardsley, P.; Newman, J.; Reith, M. E. A. Structure-Activity Relationship Studies of 4-[2-(Diphenylmethoxy)-ethyl]-1- benzylpiperidine Derivatives and their N- analogues: Evaluation of Behavioral Activity of O-and N-Analogues and their Binding to Monoamine transporters. J. Med. Chem. 2001, 44, 937-948.
    • (2001) J. Med. Chem. , vol.44 , pp. 937-948
    • Dutta, A.K.1    Fei, X.-S.2    Beardsley, P.3    Newman, J.4    Reith, M.E.A.5
  • 16
    • 0035801762 scopus 로고    scopus 로고
    • Rational Design and synthesis of novel conformationally constrained 2,5-disubstituted cis- And tras-piperidine derivatives exhibiting differential activity for the dopamine transporter
    • Dutta, A. K.; Davis, M. C.; Reith, M. E. A. Rational Design and synthesis of novel conformationally constrained 2,5-disubstituted cis- and tras-piperidine derivatives exhibiting differential activity for the dopamine transporter. Bioorg. Med. Lett. 2001, 11, 2337-2340.
    • (2001) Bioorg. Med. Lett. , vol.11 , pp. 2337-2340
    • Dutta, A.K.1    Davis, M.C.2    Reith, M.E.A.3
  • 17
    • 0037573222 scopus 로고    scopus 로고
    • Interaction of cis-(6-benzhydryl-piperidin-3-yl)- Benzyl-amine analogues with monoamine transporters: Structure Activity Relationship study of structurally constrained 3,6- disubstituted piperidine analogues of (2,2-diphenylethyl)-[1-(4- fluorobenzyl)piperidine-4-ylmethyl]amine
    • Kolhatkar, R. B.; Ghorai, S. K.; George, C.; Reith, M. E. A.; Dutta, A K. Interaction of cis-(6-benzhydryl-piperidin-3-yl)- benzyl-amine analogues with monoamine transporters: Structure Activity Relationship study of structurally constrained 3,6- disubstituted piperidine analogues of (2,2-diphenylethyl)-[1- (4- fluorobenzyl)piperidine-4-ylmethyl]amine. J. Med. Chem. 2003, 46, 2205-2215.
    • (2003) J. Med. Chem. , vol.46 , pp. 2205-2215
    • Kolhatkar, R.B.1    Ghorai, S.K.2    George, C.3    Reith, M.E.A.4    Dutta, A.K.5
  • 18
    • 0034649563 scopus 로고    scopus 로고
    • Synthesis and transporter binding properties of bridged piperazine analogues of 1-{2-[bis(4-fluorophenyl)methoxy]ethyl}-4-(3-phenylpropyl) piperazine (GBR 12909)
    • Zhang, Y.; Rothman, R. B.; Dersch, C. M.; de Costa, B. R.; Jacobson, A. E.; Rice, K. C. Synthesis and transporter binding properties of bridged piperazine analogues of 1-{2-[bis(4-fluorophenyl)methoxy]ethyl}-4-(3- phenylpropyl)piperazine (GBR 12909). J. Med. Chem. 2000, 43, 4840-4849.
    • (2000) J. Med. Chem. , vol.43 , pp. 4840-4849
    • Zhang, Y.1    Rothman, R.B.2    Dersch, C.M.3    De Costa, B.R.4    Jacobson, A.E.5    Rice, K.C.6
  • 19
    • 0037295055 scopus 로고    scopus 로고
    • Synthesis of dopamine transporter selective 3-{2- (diarylmethoxyethylidene)}-8-alkylaryl-8-azabicyclo [3.2.1] octanes
    • Bradley, A. L.; Izenwasser, S.; Wade, D.; Cararas, S.; Trudell, M. L. Synthesis of dopamine transporter selective 3-{2-(diarylmethoxyethylidene)}-8- alkylaryl-8-azabicyclo [3.2.1] octanes. Bioorg. Med. Chem. Lett. 2003, 13, 629-632.
    • (2003) Bioorg. Med. Chem. Lett. , vol.13 , pp. 629-632
    • Bradley, A.L.1    Izenwasser, S.2    Wade, D.3    Cararas, S.4    Trudell, M.L.5
  • 20
    • 0037009287 scopus 로고    scopus 로고
    • Synthesis and dopamine transporter binding affinities of 3a-benzyl-8-(diarylmethoxyethyl)-8-azabicyclo[3.2.1]- Octanes
    • Bradley, A. L.; Izenwasser, S.; Wade, D.; Klein-Stevens, C.; Zhu, N.; Trudell, M. L. Synthesis and dopamine transporter binding affinities of 3a-benzyl-8-(diarylmethoxyethyl)-8-azabicyclo[3.2.1]- octanes. Bioorg. Med. Chem. Lett. 2002, 12, 2387-2390.
    • (2002) Bioorg. Med. Chem. Lett. , vol.12 , pp. 2387-2390
    • Bradley, A.L.1    Izenwasser, S.2    Wade, D.3    Klein-Stevens, C.4    Zhu, N.5    Trudell, M.L.6
  • 21
  • 23
    • 0029873109 scopus 로고    scopus 로고
    • The design, binding affinity prediction and synthesis of macrocyclic angiotensin II AT1 and AT2 receptor antagonists
    • de Laszlo, S. E.; Glinka, T. W.; Greenlee, W. J.; Ball, R.; Nachbar, R. B.; Prendergast, K. The design, binding affinity prediction and synthesis of macrocyclic angiotensin II AT1 and AT2 receptor antagonists. Bioorg. Med. Chem. Lett. 1996, 6, 923-928.
    • (1996) Bioorg. Med. Chem. Lett. , vol.6 , pp. 923-928
    • De Laszlo, S.E.1    Glinka, T.W.2    Greenlee, W.J.3    Ball, R.4    Nachbar, R.B.5    Prendergast, K.6
  • 24
    • 0019958979 scopus 로고
    • Conformational restrictions of biologically active peptides via amino acid side chain groups
    • Hruby, V. J. Conformational restrictions of biologically active peptides via amino acid side chain groups. Life Sci. 1982, 31, 189-199.
    • (1982) Life Sci. , vol.31 , pp. 189-199
    • Hruby, V.J.1
  • 25
    • 0031024171 scopus 로고    scopus 로고
    • Experimental and computational approaches to estimate solubility and permeability in drug discovery and development settings
    • Lipinski, C. A.; Lombardo, F.; Dominy, B. W.; Feeney, P. J. Experimental and computational approaches to estimate solubility and permeability in drug discovery and development settings. Adv. Drug Dev. Rev. 1997, 23, 3-25.
    • (1997) Adv. Drug Dev. Rev. , vol.23 , pp. 3-25
    • Lipinski, C.A.1    Lombardo, F.2    Dominy, B.W.3    Feeney, P.J.4
  • 26
    • 1642328226 scopus 로고    scopus 로고
    • Surface activity profiling of drugs applied to the prediction of blood-brain berrier permeability
    • Suomalainen, P.; Johans, C.; Soderlund, T.; Rmnunen, K. J. Surface activity profiling of drugs applied to the prediction of blood-brain berrier permeability. J. Med. Chem. 2004, 47, 1783-1788.
    • (2004) J. Med. Chem. , vol.47 , pp. 1783-1788
    • Suomalainen, P.1    Johans, C.2    Soderlund, T.3    Rmnunen, K.J.4
  • 27
    • 0032714220 scopus 로고    scopus 로고
    • Polar molecular surface as a dominating determinant for oral absorption and brain penetration of drugs
    • Kelder, J.; Grootenhuis, D. J. P.; Bayada, D. M.; Delbressine, L. P.; Ploemen, J.-P. Polar molecular surface as a dominating determinant for oral absorption and brain penetration of drugs. Pharm. Res. 1999, 10, 1514-1519.
    • (1999) Pharm. Res. , vol.10 , pp. 1514-1519
    • Kelder, J.1    Grootenhuis, D.J.P.2    Bayada, D.M.3    Delbressine, L.P.4    Ploemen, J.-P.5
  • 28
    • 0037030653 scopus 로고    scopus 로고
    • Molecular properties that influence the oral bioavailability of drug candidates
    • Veber, D. F.; Johnson, S. R.; Cheng, H.-Y.; Smith, B. R.; Ward, K. W.; Kopple, K. D. Molecular properties that influence the oral bioavailability of drug candidates. J. Med. Chem. 2002, 45, 2615-2623.
    • (2002) J. Med. Chem. , vol.45 , pp. 2615-2623
    • Veber, D.F.1    Johnson, S.R.2    Cheng, H.-Y.3    Smith, B.R.4    Ward, K.W.5    Kopple, K.D.6
  • 31
    • 0035837029 scopus 로고    scopus 로고
    • Synthesis of 2/3- Acyl-3β-(substituted naphthyl)-8-azabicyclo[3.2.1] octanes and their binding affinities at dopamine and serotonin transport sites
    • Davies, H. M.; Gilliatt, V.; Kuhn, L. A.; Saikali, E.; Ren, P.; Hammond, P. S.; Sexton, T.; Childers, S. R. Synthesis of 2/3- acyl-3β-(substituted naphthyl)-8-azabicyclo[3.2.1]octanes and their binding affinities at dopamine and serotonin transport sites. J. Med. Chem. 2001, 44, 1509-1515.
    • (2001) J. Med. Chem. , vol.44 , pp. 1509-1515
    • Davies, H.M.1    Gilliatt, V.2    Kuhn, L.A.3    Saikali, E.4    Ren, P.5    Hammond, P.S.6    Sexton, T.7    Childers, S.R.8
  • 32
    • 0344837915 scopus 로고    scopus 로고
    • High affinity hydroxypiperidine analogues of 4-(2-benzhydryloxyethyl)-1- (4-fluorobenzyl)piperidine for the dopamine transporter: Stereospecific interactions in vitro and in vivo
    • Ghorai S.; Cook C. D.; Davis M.; Venkataraman S.; Beardsley P.; Reith M. E. A.; Dutta A K. High affinity hydroxypiperidine analogues of 4-(2-benzhydryloxyethyl)-1-(4-fluorobenzyl)piperidine for the dopamine transporter: Stereospecific interactions in vitro and in vivo. J. Med. Chem. 2003, 46, 1220-1228.
    • (2003) J. Med. Chem. , vol.46 , pp. 1220-1228
    • Ghorai, S.1    Cook, C.D.2    Davis, M.3    Venkataraman, S.4    Beardsley, P.5    Reith, M.E.A.6    Dutta, A.K.7
  • 33
    • 4744363792 scopus 로고    scopus 로고
    • Bruker AXS Inc., Madison, WI
    • (a)Bruker 1999. SMART v5.059. Bruker AXS Inc., Madison, WI.
    • (1999) SMART V5.059
  • 34
    • 2142819829 scopus 로고    scopus 로고
    • Bruker AXS Inc., Madison, WI
    • (b) Bruker 2000. SAINT v6.02A. Bruker AXS Inc., Madison, WI.
    • (2000) SAINT V6.02A
  • 35
    • 0004150157 scopus 로고    scopus 로고
    • Bruker AXS Inc., Madison, WI
    • (c) Bruker (2000b). SHELXTL v6.10. Bruker AXS Inc., Madison, WI.
    • (2000) SHELXTL V6.10


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