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Volumn 16, Issue 6, 2008, Pages 2769-2778

Further structural optimization of cis-(6-benzhydryl-piperidin-3-yl)-benzylamine and 1,4-diazabicyclo[3.3.1]nonane derivatives by introducing an exocyclic hydroxyl group: Interaction with dopamine, serotonin, and norepinephrine transporters

Author keywords

Cocaine; Dopamine transporter; Norepinephrine transporter; Serotonin transporter

Indexed keywords

(6 BENZHYDRYL PIPERIDIN 3 YL)BENZYLAMINE; BENZILIC ACID; BENZYLAMINE DERIVATIVE; DIAMINE; DOPAMINE TRANSPORTER; HYDROXYL GROUP; NONANE; NORADRENALIN TRANSPORTER; SEROTONIN TRANSPORTER; UNCLASSIFIED DRUG;

EID: 40949116669     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2008.01.009     Document Type: Article
Times cited : (10)

References (21)
  • 1
    • 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 (1990) 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-administration of cocaine
    • Ritz M.C., Lamb R.J., Goldberg S.R., and Kuhar M.J. Cocaine receptors on dopamine transporters are related to self-administration of cocaine. Science 237 (1987) 1219-1223
    • (1987) Science , vol.237 , pp. 1219-1223
    • Ritz, M.C.1    Lamb, R.J.2    Goldberg, S.R.3    Kuhar, M.J.4
  • 3
    • 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., and Caron M.G. Hyperlocomotion and indifference to cocaine and amphetamine in mice lacking the dopamine transporter. Nature 379 (1996) 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
  • 4
    • 0025895413 scopus 로고
    • Behavioral effects of selective dopaminergic compounds in rats discriminating cocaine injections
    • Witkin J.M., Nichols D.E., Terry P., and Katz J.L. Behavioral effects of selective dopaminergic compounds in rats discriminating cocaine injections. J. Pharmacol. Exp. Ther. 257 (1991) 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
    • 34447532025 scopus 로고    scopus 로고
    • Cocaine reward and locomotion stimulation in mice with reduced dopamine transporter expression
    • Tilley M.R., Cagniard B., Zhuang X., Han D.D., Tiao N., and Gu H.H. Cocaine reward and locomotion stimulation in mice with reduced dopamine transporter expression. BMC Neurosci. 8 (2007) 42
    • (2007) BMC Neurosci. , vol.8 , pp. 42
    • Tilley, M.R.1    Cagniard, B.2    Zhuang, X.3    Han, D.D.4    Tiao, N.5    Gu, H.H.6
  • 6
    • 0031037946 scopus 로고    scopus 로고
    • Serotonergic mechanisms involved in the discriminative stimulus, reinforcing and subjective effects of cocaine
    • Walsh S.L., and Cunningham K.A. Serotonergic mechanisms involved in the discriminative stimulus, reinforcing and subjective effects of cocaine. Psychopharmacology (Berl) 130 (1997) 41-58
    • (1997) Psychopharmacology (Berl) , vol.130 , pp. 41-58
    • Walsh, S.L.1    Cunningham, K.A.2
  • 7
    • 0030473214 scopus 로고    scopus 로고
    • Sustained decrease in cocaine-maintained responding in rhesus monkeys with 1-[2-[bis(4-fluorophenyl)methoxy]ethyl]-4-(3-hydroxy-3-phenylpropyl) piperazinyl decanoate, a long-acting ester derivative of GBR 12909
    • Glowa J.R., Fantegrossi W.E., Lewis D.B., Matecka D., Rice K.C., and Rothman R.B. Sustained decrease in cocaine-maintained responding in rhesus monkeys with 1-[2-[bis(4-fluorophenyl)methoxy]ethyl]-4-(3-hydroxy-3-phenylpropyl) piperazinyl decanoate, a long-acting ester derivative of GBR 12909. J. Med. Chem. 39 (1996) 4689-4691
    • (1996) J. Med. Chem. , vol.39 , pp. 4689-4691
    • Glowa, J.R.1    Fantegrossi, W.E.2    Lewis, D.B.3    Matecka, D.4    Rice, K.C.5    Rothman, R.B.6
  • 9
    • 33645472930 scopus 로고    scopus 로고
    • Development of the dopamine transporter selective RTI-336 as a pharmacotherapy for cocaine abuse
    • Carroll F.I., Howard J.L., Howell L.L., Fox B.S., and Kuhar M.J. Development of the dopamine transporter selective RTI-336 as a pharmacotherapy for cocaine abuse. Aaps J. 8 (2006) E196-E203
    • (2006) Aaps J. , vol.8
    • Carroll, F.I.1    Howard, J.L.2    Howell, L.L.3    Fox, B.S.4    Kuhar, M.J.5
  • 10
    • 40949126731 scopus 로고    scopus 로고
    • Distinctions between dopamine transporter antagonists could be just around the bend
    • Henry L.K., and Blakely R.D. Distinctions between dopamine transporter antagonists could be just around the bend. Mol. Pharmacol. (2007)
    • (2007) Mol. Pharmacol.
    • Henry, L.K.1    Blakely, R.D.2
  • 12
    • 0242408732 scopus 로고    scopus 로고
    • Dopamine transporter as target for drug development of cocaine dependence medications
    • Dutta A.K., Zhang S., Kolhatkar R., and Reith M.E. Dopamine transporter as target for drug development of cocaine dependence medications. Eur. J. Pharmacol. 479 (2003) 93-106
    • (2003) Eur. J. Pharmacol. , vol.479 , pp. 93-106
    • Dutta, A.K.1    Zhang, S.2    Kolhatkar, R.3    Reith, M.E.4
  • 13
    • 0030043953 scopus 로고    scopus 로고
    • Structure-activity relationship studies of novel 4-[2-[bis(4-fluorophenyl)methoxy]ethyl]-1-(3-phenylpropyl)piperidine analogs: synthesis and biological evaluation at the dopamine and serotonin transporter sites
    • Dutta A.K., Xu C., and Reith M.E. Structure-activity relationship studies of novel 4-[2-[bis(4-fluorophenyl)methoxy]ethyl]-1-(3-phenylpropyl)piperidine analogs: synthesis and biological evaluation at the dopamine and serotonin transporter sites. J. Med. Chem. 39 (1996) 749-756
    • (1996) J. Med. Chem. , vol.39 , pp. 749-756
    • Dutta, A.K.1    Xu, C.2    Reith, M.E.3
  • 14
    • 0031021652 scopus 로고    scopus 로고
    • Highly selective, novel analogs 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., and Reith M.E. Highly selective, novel analogs of 4-[2-(diphenylmethoxy)ethyl]-1-benzylpiperidine for the dopamine transporter: effect of different aromatic substitutions on their affinity and selectivity. J. Med. Chem. 40 (1997) 35-43
    • (1997) J. Med. Chem. , vol.40 , pp. 35-43
    • Dutta, A.K.1    Coffey, L.L.2    Reith, M.E.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 O- and N-analogues and their binding to monoamine transporters
    • Dutta A.K., Fei X.S., Beardsley P.M., Newman J.L., and Reith M.E. Structure-activity relationship studies of 4-[2-(diphenylmethoxy)ethyl]-1-benzylpiperidine derivatives and their N-analogues: evaluation of O- and N-analogues and their binding to monoamine transporters. J. Med. Chem. 44 (2001) 937-948
    • (2001) J. Med. Chem. , vol.44 , pp. 937-948
    • Dutta, A.K.1    Fei, X.S.2    Beardsley, P.M.3    Newman, J.L.4    Reith, M.E.5
  • 16
    • 0035801762 scopus 로고    scopus 로고
    • Rational design and synthesis of novel 2,5-disubstituted cis- and trans-piperidine derivatives exhibiting differential activity for the dopamine transporter
    • Dutta A.K., Davis M.C., and Reith M.E. Rational design and synthesis of novel 2,5-disubstituted cis- and trans-piperidine derivatives exhibiting differential activity for the dopamine transporter. Bioorg. Med. Chem. Lett. 11 (2001) 2337-2340
    • (2001) Bioorg. Med. Chem. Lett. , vol.11 , pp. 2337-2340
    • Dutta, A.K.1    Davis, M.C.2    Reith, M.E.3
  • 17
    • 0037573222 scopus 로고    scopus 로고
    • Interaction of cis-(6-benzhydrylpiperidin-3-yl)benzylamine analogues with monoamine transporters: structure-activity relationship study of structurally constrained 3,6-disubstituted piperidine analogues of (2,2-diphenylethyl)-[1-(4-fluorobenzyl)piperidin-4-ylmethyl]amine
    • Kolhatkar R.B., Ghorai S.K., George C., Reith M.E., and Dutta A.K. Interaction of cis-(6-benzhydrylpiperidin-3-yl)benzylamine analogues with monoamine transporters: structure-activity relationship study of structurally constrained 3,6-disubstituted piperidine analogues of (2,2-diphenylethyl)-[1-(4-fluorobenzyl)piperidin-4-ylmethyl]amine. J. Med. Chem. 46 (2003) 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.4    Dutta, A.K.5
  • 18
    • 4744375699 scopus 로고    scopus 로고
    • 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
    • Kolhatkar R., Cook C.D., Ghorai S.K., Deschamps J., Beardsley P.M., Reith M.E., and Dutta A.K. 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. J. Med. Chem. 47 (2004) 5101-5113
    • (2004) J. Med. Chem. , vol.47 , pp. 5101-5113
    • Kolhatkar, R.1    Cook, C.D.2    Ghorai, S.K.3    Deschamps, J.4    Beardsley, P.M.5    Reith, M.E.6    Dutta, A.K.7
  • 19
    • 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.K., Cook C., Davis M., Venkataraman S.K., George C., Beardsley P.M., Reith M.E., and 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. 46 (2003) 1220-1228
    • (2003) J. Med. Chem. , vol.46 , pp. 1220-1228
    • Ghorai, S.K.1    Cook, C.2    Davis, M.3    Venkataraman, S.K.4    George, C.5    Beardsley, P.M.6    Reith, M.E.7    Dutta, A.K.8
  • 20
    • 0037138704 scopus 로고    scopus 로고
    • Highly selective hydrolytic kinetic resolution of terminal epoxides catalyzed by chiral (salen)Co(III) complexes. Practical synthesis of enantioenriched terminal epoxides and 1,2-diols
    • Schaus S.E., Brandes B.D., Larrow J.F., Tokunaga M., Hansen K.B., Gould A.E., Furrow M.E., and Jacobsen E.N. Highly selective hydrolytic kinetic resolution of terminal epoxides catalyzed by chiral (salen)Co(III) complexes. Practical synthesis of enantioenriched terminal epoxides and 1,2-diols. J. Am. Chem. Soc. 124 (2002) 1307-1315
    • (2002) J. Am. Chem. Soc. , vol.124 , pp. 1307-1315
    • Schaus, S.E.1    Brandes, B.D.2    Larrow, J.F.3    Tokunaga, M.4    Hansen, K.B.5    Gould, A.E.6    Furrow, M.E.7    Jacobsen, E.N.8
  • 21
    • 22844451687 scopus 로고    scopus 로고
    • Discovery of novel trisubstituted asymmetric derivatives of (2S,4R,5R)-2-benzhydryl-5-benzylaminotetrahydropyran-4-ol, exhibiting high affinity for serotonin and norepinephrine transporters in a stereospecific manner
    • Zhang S., Zhen J., Reith M.E., and Dutta A.K. Discovery of novel trisubstituted asymmetric derivatives of (2S,4R,5R)-2-benzhydryl-5-benzylaminotetrahydropyran-4-ol, exhibiting high affinity for serotonin and norepinephrine transporters in a stereospecific manner. J. Med. Chem. 48 (2005) 4962-4971
    • (2005) J. Med. Chem. , vol.48 , pp. 4962-4971
    • Zhang, S.1    Zhen, J.2    Reith, M.E.3    Dutta, A.K.4


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.