Positron labeled analogs of TCP: Synthesis of 1−[4−[18F]fluoromethyl-1−(2-thienyl)cyclohexyl]piperidine

Maëda, Minoru; Tsukiyama, Syuji; Fukumura, Toshimitsu; Orita, Kazuhiro; Kojima, Masayasu

doi:10.1016/0883-2889(91)90163-u

Cited by 6 publications

(3 citation statements)

References 23 publications

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“…Its in vivo brain distribution did not match the in vitro distribution of TCP binding sites [36]. The radiolabelling of cis-and trans-[ 18 F]6 was developped by nucleophilic fluorination from the tosylate or mesylate precursor, but no biological data were reported for those radioligands [35]. The 4-fluoropiperidine derivative 7 demonstrated a K i of 26 nM for NMDARs in competitive in vitro binding assay versus [ 3 H]TCP [37].…”

Section: Radiolabelled Pcp or Tcp Analogues For Petmentioning

confidence: 98%

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PET and SPECT Imaging of the NMDA Receptor System: An Overview of Radiotracer Development

Sobrio¹,

Gilbert²,

Perrio³

et al. 2010

MRMC

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Imaging the N-methyl-D-aspartate receptors (NMDARs) in the living human brain by positron emission tomography (PET) or single photon emission computed tomography (SPECT) would provide useful information on the role of these receptors in ischemia and in various neurological disorders such as degenerative diseases, epilepsy or schizophrenia. To assess NMDAR radiotracer development and to propose perspectives, we overviewed the PET and SPECT candidate radioligands developed until now. Labelled molecules of interest were classified in three groups according to their binding site: intrachannel pore site blockers, glycine site inhibitors and NR2B selective subunit antagonists.

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Section: Radiolabelled Pcp or Tcp Analogues For Petmentioning

confidence: 98%

“…(2)). First, TCP analogues bearing a fluoromethyl group on the piperidine ring ([ 18 F]5) or on the cyclohexyl moiety ([ 18 F]6) were radiolabelled by nucleophilic substitution with fluoride-18 anion from the mesylate precursor [34,35]. [ 18 F]5 was obtained with a specific radioactivity of 27 GBq/ mol.…”

Section: Radiolabelled Pcp or Tcp Analogues For Petmentioning

confidence: 99%

PET and SPECT Imaging of the NMDA Receptor System: An Overview of Radiotracer Development

Sobrio¹,

Gilbert²,

Perrio³

et al. 2010

MRMC

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“…Ligands for the EAA receptors which have previously been labelled with positron-emitting radionuclides have been non-competitive NMDA (N-methyl-D-aspartate) antagonists: [I ICIketamine (1) as well as 11C-and 18F-analogues of MK-801 (2-5), phencyclidine (6) and thienylcyclohexylpiperidine (7)(8)(9). A number of substituted 2,3-dihydroxyquinoxalines (quinoxaline-2,3-dione) have been shown (10) to be antagonists of the E A A receptors: 6,7-dichloro-2,3-dihydroxyquinoxaline (DCQX), 6,7-dinitro-2,3-dihydroxyquinoxaline (DNQX), 6-cyano-7-nitro-2,3-dihydroxyquinoxaline (CNQX) and 6-nitro-7-sulfamoylbenzo[Oquinoxaline-2,3-dione (NBQX).These substances have moderately high affinities for non-NMDA receptors (IC5os for (10)).…”

Section: Introductionmentioning

confidence: 99%

Synthesis of [2‐¹¹C]‐6,7‐dichloro‐2,3‐dihydroxyquinoxaline and evaluation of its in in vivo distribution in rat with PET

Thorell¹,

Stone‐Elander²,

Ingvar³

et al. 1995

Labelled Comp Radiopharmac

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A method for labelling 6,7-dichloro-2,3-dihydroxyquinoxaline (DCQX) in position 2 with carbon-1 1 is presented. Diethyl [l-l1C]oxalate was synthesized in a two-step, microwave-assisted procedure from no-camer-added [ 1 Wlcyanide and was reacted with 4,5-dichloro-l,2-phenylenediamine in sulfuric acid at ISOOC for 10 min. [2-1 ICIDCQX, isolated by semi-preparative HPLC, was >99% radiochemically pure with a specific activity ranging between 19 -26 TBq/mmol. The total time of synthesis was 45-55 min and the isolated, decay-corrected yields were on the order of lo%, based on the trapped [IlCIcyanide. A PET study of its biodistribution after intravenous injection in a male rat revealed that the extraction of [2-* ICIDCQX across the intact blood-brain barrier was 12%.

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Syntheses and Uses of Isotopically Labelled Organic Halides

Zieliński

Kańska

2009

Patai's Chemistry of Functional Groups

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Introduction Syntheses and Uses of Organic Halides Labelled with Fluorine‐18 and Carbon‐11 Syntheses and Uses of Isotopically Labelled Organic Chlorides Syntheses and Applications of Bromine Isotopes Syntheses and Uses of Organic Compounds Labelled with Iodine Isotopes Syntheses of Organic Compounds Labelled with Astatine‐211 Isotope Effect Studies with Organic Halides Acknowledgements

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Positron labeled analogs of TCP: Synthesis of 1−[4−[18F]fluoromethyl-1−(2-thienyl)cyclohexyl]piperidine

Cited by 6 publications

References 23 publications

PET and SPECT Imaging of the NMDA Receptor System: An Overview of Radiotracer Development

PET and SPECT Imaging of the NMDA Receptor System: An Overview of Radiotracer Development

Synthesis of [2‐¹¹C]‐6,7‐dichloro‐2,3‐dihydroxyquinoxaline and evaluation of its in in vivo distribution in rat with PET

Syntheses and Uses of Isotopically Labelled Organic Halides

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Positron labeled analogs of TCP: Synthesis of 1−[4−[18F]fluoromethyl-1−(2-thienyl)cyclohexyl]piperidine

Cited by 6 publications

References 23 publications

PET and SPECT Imaging of the NMDA Receptor System: An Overview of Radiotracer Development

PET and SPECT Imaging of the NMDA Receptor System: An Overview of Radiotracer Development

Synthesis of [2‐11C]‐6,7‐dichloro‐2,3‐dihydroxyquinoxaline and evaluation of its in in vivo distribution in rat with PET

Syntheses and Uses of Isotopically Labelled Organic Halides

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Synthesis of [2‐¹¹C]‐6,7‐dichloro‐2,3‐dihydroxyquinoxaline and evaluation of its in in vivo distribution in rat with PET