A novel one-pot palladium-mediated synthesis of N-[(2-hydroxyphenyl)methyl]-N-(4-phenoxy-3-pyridinyl) acetamide, the precursor to [11C]PBR28, a PET biomarker for the peripheral benzodiazepine receptor

被引：3

作者：

Hoareau, Raphael ^{[1
]}

Scott, Peter J. H. ^{[1
]}

机构：

[1] Univ Michigan, Dept Radiol, Ann Arbor, MI 48109 USA

来源：

TETRAHEDRON LETTERS | 2010年 / 51卷 / 26期

关键词：

C-11]PBR28; Positron emission tomography; Radiopharmaceutical synthesis; POSITRON-EMISSION-TOMOGRAPHY; PROTEIN; 18; KDA; IN-VIVO; STANNOUS CHLORIDE; HUMAN BRAIN; BINDING; RADIOLIGAND; C-11; RADIOSYNTHESIS; TOXICITY;

D O I：

10.1016/j.tetlet.2010.04.089

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Due to an urgent need to image the peripheral benzodiazepine receptor (PBR) in living human subjects using positron emission tomography imaging, we had cause to prepare N-[(2-hydroxyphenyl)methyl]-N-(4-phenoxy-3-pyridinyl) acetamide (desmethyl-PBR28 (1)), the precursor to [C-11]PBR28. Herein, we report a new synthesis of the precursor in which palladium-mediated reduction of the nitro pyridine to the corresponding amino pyridine, and subsequent reductive amination, can be achieved with decaborane in a convenient one-pot procedure. This procedure is operationally simpler than the current alternatives and provides high quality precursor suitable for use in clinical applications. (C) 2010 Elsevier Ltd. All rights reserved.

引用

页码：3353 / 3355

页数：3

共 11 条

[1] Synthesis and in vivo evaluation of (E)-N-[11C]methyl-4-(3-pyridinyl)-3-butene-1-amine ([11C]metanicotine) as a nicotinic receptor radioligand
Brown-Proctor, C
Snyder, SE
Sherman, PS
Kilbourn, MR
NUCLEAR MEDICINE AND BIOLOGY, 2000, 27 (04) : 415 - 418
[2] Radiosynthesis of 2-[6-chloro-2-(4-iodophenyl)imidazo [1,2-a]pyridin-3-yl]-N-ethyl-N-[11C]methyl-acetamide, [11C]CLINME, a novel radioligand for imaging the peripheral benzodiazepine receptors with PET
Thominiaux, C.
Mattner, F.
Greguric, I.
Boutin, H.
Chauveau, F.
Kuhnast, B.
Gregoire, M.-C.
Loc'h, C.
Valette, H.
Bottlaender, M.
Hantraye, Ph.
Tavitian, B.
Katsifis, A.
Dolle, F.
JOURNAL OF LABELLED COMPOUNDS & RADIOPHARMACEUTICALS, 2007, 50 (3-4): : 229 - 236
[3] Facile synthesis and PET imaging of a novel potential heart acetylcholinesterase tracer N-[11C]methyl-3-[[(dimethylamino)carbonyl]oxy]-2-(2′2′-diphenylpropionoxymethyl)pyridinium
Wang, JQ
Miller, MA
Mock, BH
Lopshire, JC
Groh, WJ
Zipes, DP
Hutchins, GD
Zheng, QH
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2005, 15 (20) : 4510 - 4514
[4] Radiosynthesis of 7-chloro-N,N-dimethyl-5-[11C]methyl-4-oxo-3-phenyl-3,5-dihydro-4H-pyridazino[4,5-b]indole-1-acetamide, [11C]SSR180575, a novel radioligand for imaging the TSPO (peripheral benzodiazepine receptor) with PET
Thominiaux, Cyrille
Damont, Annelaure
Kuhnast, Bertrand
Demphel, Stephane
Le Helleix, Stephane
Boisnard, Sabine
Rivron, Luc
Chauveau, Fabien
Boutin, Herve
Van Camp, Nadia
Boisgard, Raphael
Roy, Sebastien
Allen, John
Rooney, Thomas
Benavides, Jesus
Hantraye, Philippe
Tavitian, Bertrand
Dolle, Frederic
JOURNAL OF LABELLED COMPOUNDS & RADIOPHARMACEUTICALS, 2010, 53 (13-14): : 767 - 773
[5] Synthesis of 1-(2,4-dichlorophenyl)-4-cyano-5-(4[11C]methoxyphenyl)-N-(piperidin-1-yl)-1H-pyrazole-3-carboxamide ([11C]JHU75528) and 1-(2bromophenyl)-4-cyano-5-(4-[11C]methoxyphenyl)-N-(piperidin-1-yl)-1H-pyrazole-3-carboxamide ([11C]JHU75575) as potential radioligands for PET imaging of cerebral cannabinoid receptor
Fan, Hong
Ravert, Hayden T.
Holt, Daniel P.
Dannals, Robert F.
Horti, Andrew G.
JOURNAL OF LABELLED COMPOUNDS & RADIOPHARMACEUTICALS, 2006, 49 (12): : 1021 - 1036
[6] Synthesis of (R)- and (S)-[O-methyl-11C]N-[2-[3-(2-cyano-phenoxy)-2-hydroxy-propylamino]-ethyl]-N′-(4-methoxy-phenyl)-urea as candidate high affinity β1-adrenoceptor PET radioligands
Wagner, S
Law, MP
Riemann, B
Pike, VW
Breyholz, HJ
Höltke, C
Faust, A
Schober, O
Schäfers, M
Kopka, K
JOURNAL OF LABELLED COMPOUNDS & RADIOPHARMACEUTICALS, 2005, 48 (10): : 721 - 733
[7] SYNTHESIS AND RADIOLABELING OF N-[4-[4-(2-[11C]METHOXYPHENYL)PIPERAZIN-1-YL]BUTYL] BENZO[b]THIOPHENE-2-CARBOXAMIDE, A POTENTIAL RADIOTRACER FOR D3 RECEPTOR IMAGING WITH PET
Kuhnast, B.
Demphel, S.
Besret, L.
Coulon, C.
Ottaviani, M.
Guillermier, M.
Valette, H.
Bottlaender, M.
Dolle, F.
JOURNAL OF LABELLED COMPOUNDS & RADIOPHARMACEUTICALS, 2005, 48 : S166 - S166
[8] Synthesis and radiolabeling of N-[4-[4-(2-[11C]methoxyphenyl)piperazin-1-yl]butyl]benzo[b]thiophene-2-carboxamide -: a potential radiotracer for D3 receptor imaging with PET
Kuhnast, Bertrand
Valette, Heric
Besret, Laurent
Demphel, Stephane
Coulon, Christine
Ottaviani, Michele
Guillermier, Martine
Bottlaender, Michel
Dolle, Fredreic
NUCLEAR MEDICINE AND BIOLOGY, 2006, 33 (06) : 785 - 795
[9] Synthesis and preclinical evaluation of carbon-11 labelled N-((5-(4-fluoro-2-[11C]methoxyphenyl) pyridin-3-yl) methyl) cyclopentanamine as a PET tracer for NR2B subunit-containing NMDA receptors
Christiaans, Johannes A. M.
Klein, Pieter J.
Metaxas, Athanasios
Kooijman, Esther J. M.
Schuit, Robert C.
Leysen, Josee E.
Lammertsma, Adriaan A.
van Berckel, Bart N. M.
Windhorst, Albert D.
NUCLEAR MEDICINE AND BIOLOGY, 2014, 41 (08) : 670 - 680
[10] One-pot synthesis of substituted pyrrolo[3,4-b]pyridine-4,5-diones based on the reaction of N-(1-(4-hydroxy-6-methyl-2-oxo-2H-pyran-3-yl)-2-oxo-2-arylethyl)acetamide with amines
Melekhina, Valeriya G.
Komogortsev, Andrey N.
Lichitsky, Boris, V
Mityanov, Vitaly S.
Fakhrutdinov, Artem N.
Dudinov, Arkady A.
Migulin, Vasily A.
Nelyubina, Yulia, V
Melnikova, Elizaveta K.
Krayushkin, Michail M.
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2019, 15 : 2840 - 2846

← 1 2 →