메뉴 건너뛰기




Volumn 48, Issue 22, 2005, Pages 7080-7083

Synthesis, radiosynthesis, and biological evaluation of carbon-11 and fluorine-18 (N-fluoroalkyl) labeled 2β-carbomethoxy-3β-(4′-(3- furyl)phenyl)-tropanes and -nortropanes: Candidate radioligands for in vivo imaging of the serotonin transporter with positron emission tomography

Author keywords

[No Author keywords available]

Indexed keywords

2BETA CARBOMETHOXY 3BETA [4' (3 FURYL)PHENYL]NORTROPANE C 11; 3BETA (4 IODOPHENYL) 2BETA TROPANECARBOXYLIC ACID METHYL ESTER; CARBON 11; DOPAMINE TRANSPORTER; FLUORINE 18; N (2 FLUOROETHYL) 2BETA CARBOMETHOXY 3BETA [4' (3 FURYL)PHENYL]NORTROPANE F 18; N (3 FLUOROPROPYL) 2BETA CARBOMETHOXY 3BETA [4' (3 FURYL)PHENYL]NORTROPANE; N (4 FLUOROBUTYL) 2BETA CARBOMETHOXY 3BETA [4' (3 FURYL)PHENYL]NORTROPANE; N METHYL 2BETA CARBOMETHOXY 3BETA [4' (3 FURYL)PHENYL]TROPANE C 11; NORADRENALIN TRANSPORTER; NORTROPANE DERIVATIVE; SEROTONIN TRANSPORTER; TROPANE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 27444439092     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm0504095     Document Type: Article
Times cited : (15)

References (18)
  • 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
    • 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
  • 3
    • 0038416872 scopus 로고    scopus 로고
    • 2002 Medicinal Chemistry Division Award Address: Monoamine transporters and opioid receptors. Targets for addiction therapy
    • Carroll, F. I. 2002 Medicinal Chemistry Division Award Address: Monoamine Transporters and Opioid Receptors. Targets for Addiction Therapy. J. Med. Chem. 2003, 46, 1775-1794.
    • (2003) J. Med. Chem. , vol.46 , pp. 1775-1794
    • Carroll, F.I.1
  • 4
    • 0028773367 scopus 로고
    • Secondary amine analogues of 3β-(4′-Substituted 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.; Carroll, F. I. Secondary Amine Analogues of 3β-(4′-Substituted phenyl)tropane-2β-carboxylic Acid Esters and N-Norcocaine Exhibit Enhanced Affinity for Serotonin and Norepinephrine Transporters. J. Med. Chem. 1994, 37, 1220-1223.
    • (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
  • 5
    • 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 fore-brain
    • Neumeyer, J. L.; Tamagnan, G.; Wang, S.; Gao, Y.; Milius, R. A.; Kula, N. S.; 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 Fore-brain. J. Med. Chem. 1996, 39, 543-548.
    • (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
  • 7
    • 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.; 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. 1996, 39, 4027-4035.
    • (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
  • 8
    • 0034698895 scopus 로고    scopus 로고
    • Synthesis and monoamine transporter affinity of 2β-carbomethoxy- 3β-(2″-, 3″- or 4″-substituted) biphenyltropanes
    • Tamagnan, G.; Baldwin, R. M.; Kula, N. S.; Baldessarini, R. J.; Innis, R. B. Synthesis and Monoamine Transporter Affinity of 2β-Carbomethoxy- 3β-(2″-, 3″- or 4″-substituted) Biphenyltropanes. Bioorg. Med. Chem. Lett. 2000, 10, 1783-1785.
    • (2000) Bioorg. Med. Chem. Lett. , vol.10 , pp. 1783-1785
    • Tamagnan, G.1    Baldwin, R.M.2    Kula, N.S.3    Baldessarini, R.J.4    Innis, R.B.5
  • 9
    • 1242273831 scopus 로고    scopus 로고
    • Synthesis, radiosynthesis, and biological evaluation of carbon-11 and iodine-123 labeled 2β-carbomethoxy-3β-[4′-((Z)-2-halo-ethenyl) phenyl]tropanes: Candidate radioligands for in vivo imaging of the serotonin transporter
    • Plisson, C.; McConathy, J.; Martarello, L.; Malveaux, E. J.; Camp, V. M.; Williams, L.; Votaw, J. R.; Goodman, M. M. Synthesis, Radiosynthesis, and Biological Evaluation of Carbon-11 and Iodine-123 Labeled 2β-Carbomethoxy- 3β-[4′-((Z)-2-halo-ethenyl)phenyl]tropanes: Candidate Radioligands for in Vivo Imaging of the Serotonin Transporter. J. Med. Chem. 2004, 47, 1122-1135.
    • (2004) J. Med. Chem. , vol.47 , pp. 1122-1135
    • Plisson, C.1    McConathy, J.2    Martarello, L.3    Malveaux, E.J.4    Camp, V.M.5    Williams, L.6    Votaw, J.R.7    Goodman, M.M.8
  • 11
    • 0035803004 scopus 로고    scopus 로고
    • Synthesis and biological evaluation of a series of novel N- or O-Fluoroalkyl derivatives of tropane: Potential Positron Emission Tomography (PET) imaging agents for the dopamine transporter
    • Gu, X.-H.; Zong, R.; Kula, N. S.; Baldessarini, R. J.; Neumeyer, J. L. Synthesis and Biological Evaluation of a Series of Novel N- or O-Fluoroalkyl Derivatives of Tropane: Potential Positron Emission Tomography (PET) Imaging Agents for the Dopamine Transporter. Bioorg. Med. Chem. Lett. 2001, 11, 3049-3053.
    • (2001) Bioorg. Med. Chem. Lett. , vol.11 , pp. 3049-3053
    • Gu, X.-H.1    Zong, R.2    Kula, N.S.3    Baldessarini, R.J.4    Neumeyer, J.L.5
  • 12
    • 1842640037 scopus 로고    scopus 로고
    • Synthesis and monoamine transporter affinity of 3′-Analogs of 2-β-Carbomethoxy-3-β-(4′-iodophenyl)-tropane (β-CIT)
    • Bois, F.; Baldwin, R. M.; Kula, N. S.; Baldessarini, R. J.; Innis, R. B.; Tamagnan, G. Synthesis and Monoamine Transporter Affinity of 3′-Analogs of 2-β-Carbomethoxy-3-β-(4′-iodophenyl)-tropane (β-CIT). Bioorg. Med. Chem. Lett. 2004, 14, 2117-2120.
    • (2004) Bioorg. Med. Chem. Lett. , vol.14 , pp. 2117-2120
    • Bois, F.1    Baldwin, R.M.2    Kula, N.S.3    Baldessarini, R.J.4    Innis, R.B.5    Tamagnan, G.6
  • 13
    • 16244410784 scopus 로고    scopus 로고
    • Synthesis and monoamine transporter affinity of new 2β-Carbomethoxy- 3β-[4-(substituted thiophenyl)]phenyltropanes: Discovery of a selective SERT antagonist with picomolar potency
    • Tamagnan, G.; Alagille, D.; Fu, X.; Kula, N. S.; Baldessarini, R. J.; Innis, R. B.; Baldwin, R. M. Synthesis and Monoamine Transporter Affinity of New 2β-Carbomethoxy-3β-[4-(substituted thiophenyl)]phenyltropanes: Discovery of a Selective SERT Antagonist with Picomolar Potency. Bioorg. Med. Chem. Lett. 2005, 15, 1131-1133.
    • (2005) Bioorg. Med. Chem. Lett. , vol.15 , pp. 1131-1133
    • Tamagnan, G.1    Alagille, D.2    Fu, X.3    Kula, N.S.4    Baldessarini, R.J.5    Innis, R.B.6    Baldwin, R.M.7
  • 14
    • 37049089033 scopus 로고
    • The chemistry of organolead(IV) tricarboxylates. Synthesis and electrophilic heteroarylation reactions of 2- and 3-Thienyl-, and 2- and 3-Furyl-lead tricarboxylates
    • Pinhey, J. T.; Roche, E. G. The Chemistry of Organolead(IV) Tricarboxylates. Synthesis and Electrophilic Heteroarylation Reactions of 2- and 3-Thienyl-, and 2- and 3-Furyl-lead Tricarboxylates. J. Chem. Soc., Perkin Trans. 1 1988, 2415-2421.
    • (1988) J. Chem. Soc., Perkin Trans. 1 , pp. 2415-2421
    • Pinhey, J.T.1    Roche, E.G.2
  • 15
    • 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
  • 16
    • 0032950927 scopus 로고    scopus 로고
    • Solid phase extraction. An alternative to the use of rotary evaporators for solvent removal in the rapid formulation of PET radiopharmaceuticals
    • Lemaire, C.; Plenevaux, A.; Aerts, J.; Del Fiore, G.; Brihaye, C.; Le Bars, D.; Comar, D.; Luxen, A. Solid Phase Extraction. An Alternative to the Use of Rotary Evaporators for Solvent Removal in the Rapid Formulation of PET Radiopharmaceuticals. J. Labelled Compd. Radiopharm. 1999, 42, 63-75.
    • (1999) J. Labelled Compd. Radiopharm. , vol.42 , pp. 63-75
    • Lemaire, C.1    Plenevaux, A.2    Aerts, J.3    Del Fiore, G.4    Brihaye, C.5    Le Bars, D.6    Comar, D.7    Luxen, A.8
  • 17
    • 0033619983 scopus 로고    scopus 로고
    • Radiosynthesis of carbon-11 labelled N-Methyl-2-(arylthio)benzylamines: Potential radiotracers for the serotonin reuptake receptor
    • Wilson, A. A.; Houle, S. Radiosynthesis of Carbon-11 Labelled N-Methyl-2-(arylthio)benzylamines: Potential Radiotracers for the Serotonin Reuptake Receptor. J. Labelled Compd. Radiopharm. 1999, 42, 1277-1288.
    • (1999) J. Labelled Compd. Radiopharm. , vol.42 , pp. 1277-1288
    • Wilson, A.A.1    Houle, S.2
  • 18
    • 13844317450 scopus 로고    scopus 로고
    • Regional distribution of serotonin transporter protein in postmortem human brain. Is the cerebellum a SERT-Free brain region?
    • Kish, S. J.; Furukawa, Y.; Chang, L.-J.; Tong, J.; Ginovart, N.; Wilson, A.; Houle, S.; Meyer, J. H. Regional Distribution of Serotonin Transporter Protein in Postmortem Human Brain. Is the Cerebellum a SERT-Free Brain Region? Nucl. Med. Biol. 2005, 32, 123-128.
    • (2005) Nucl. Med. Biol. , vol.32 , pp. 123-128
    • Kish, S.J.1    Furukawa, Y.2    Chang, L.-J.3    Tong, J.4    Ginovart, N.5    Wilson, A.6    Houle, S.7    Meyer, J.H.8


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.