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作为β-肾上腺素能受体首选放射性配体的S-(3'-叔丁基氨基-2'-羟基丙氧基)-苯并咪唑-2-[11C]酮（S-[11C]CGP 12177）自动放射性合成前体的不对称合成。

Asymmetric synthesis of a precursor for the automated radiosynthesis of S-(3'-t-butylamino-2'-hydroxypropoxy)-benzimidazol-2-[11C]one (S-[11C]CGP 12177) as a preferred radioligand for beta-adrenergic receptors.

作者信息

Brady F, Luthra S K, Tochon-Danguy H J, Steel C J, Waters S L, Kensett M J, Landais P, Shah F, Jaeggi K A, Drake A

机构信息

MRC Cyclotron Unit, Hammersmith Hospital, London, England.

出版信息

Int J Rad Appl Instrum A. 1991;42(7):621-8. doi: 10.1016/0883-2889(91)90032-v.

DOI:10.1016/0883-2889(91)90032-v
PMID:1685153
Abstract

S-[1-(2,3-Diaminophenoxy)]-3'-(N-t-butylamino)propan-2'-ol has been synthesized in three steps from 2,3-dinitro-phenol and the chiral auxiliary, S-glycidyl-3-nitrobenzenesulphonate, to provide a precursor for labelling S-(3'-t-butylamino-2'-hydroxypropoxy)-benzimidazol-2-one (S-CGP 12177) with the short-lived positron-emitting radionuclide, carbon-11 (t 1/2 = 20.4 min; beta+ = 99.8%). Reaction of the diamine with [11C]phosgene, itself derived from no-carrier-added cyclotron-produced [11C]methane, provides radiochemically and chemically pure S-[carbonyl-11C]CGP 12177 in greater than 95% enantiomeric excess after HPLC. Automated apparatus is described for safely producing up to 5.9 GBq (160 mCi) of S-[11C]CGP 12177 with high sp. act. (20-40 GBq/mu mol or 0.54-1.08 Ci/mu mol) in a form suitable for human intravenous injection at only 30 min from the end of radionuclide production. S-[11C]CGP 12177 is preferred to the formerly described racemate as a radioligand for the study of beta-adrenergic receptors in vivo by positron emission tomography.

摘要

S-[1-(2,3-二氨基苯氧基)]-3'-(N-叔丁基氨基)丙-2'-醇已由2,3-二硝基苯酚和手性助剂S-缩水甘油基-3-硝基苯磺酸盐经三步合成，以提供一种前体，用于用短寿命正电子发射放射性核素碳-11（半衰期t1/2 = 20.4分钟；β+ = 99.8%）标记S-(3'-叔丁基氨基-2'-羟基丙氧基)-苯并咪唑-2-酮（S-CGP 12177）。二胺与[11C]光气反应，[11C]光气本身源自无载体回旋加速器产生的[11C]甲烷，经高效液相色谱后，可提供放射化学和化学纯的对映体过量大于95%的S-[羰基-11C]CGP 12177。描述了一种自动化装置，该装置能够安全地生产高达5.9 GBq（160 mCi）的高比活度（20 - 40 GBq/μmol或0.54 - 1.08 Ci/μmol）的S-[11C]CGP 12177，其形式适合在放射性核素生产结束后仅30分钟进行人体静脉注射。作为正电子发射断层扫描体内研究β-肾上腺素能受体的放射性配体，S-[11C]CGP 12177比先前描述的外消旋体更受青睐。

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