氟化苯甲酰胺类抗精神病药物——2. （S）-N-[(1-乙基-2-吡咯烷基)甲基]-5-(3-[¹⁸F]氟丙基)-3-取代-2-甲氧基苯甲酰胺的合成与放射性合成
Fluorinated benzamide neuroleptics--2. Synthesis and radiosynthesis of (S)-N-[(1-ethyl-2-pyrrolidinyl)methyl]-5-(3-[18F]fluoropropyl)-3- substituted-2-methoxybenzamides.
作者信息
Mukherjee J
机构信息
Department of Radiology, University of Chicago, IL 60637.
出版信息
Int J Rad Appl Instrum A. 1991;42(8):713-21. doi: 10.1016/0883-2889(91)90174-y.
Synthesis of a fluorinated benzamide neuroleptic, (S)-N-[(1-ethyl-2- pyrrolidinyl)methyl]-5-(3-fluoropropyl)-2,3- dimethoxybenzamide starting from 3-(3,4-dimethoxyphenyl)-1-propanol in 20-25% overall yield is reported. Radiosynthesis of (S)-N-[(1-ethyl-2-pyrrolidinyl)methyl]- 5-(3[18F]fluoropropyl)-2-methoxybenzamide([18F]FPHB) and (S)-N-[(1-ethyl-2-pyrrolidinyl)methyl]-5-(3[18F]fluoropropyl)-2,3- dimethoxybenzamide([18F]FPHB) was carried out by nucleophilic substitution reaction of (S)-N-[(1-ethyl-2-pyrrolidinyl)methyl-5-(3-tosyloxypropyl)-2-me tho xybenzamide and (S)-N-[(1-ethyl-2-pyrrolidinyl)methyl]-5-(3-tosyloxypropyl)-2,3- dimethoxybenzamide respectively, with no carrier added [18F]fluoride. Both, [18F]FPHB and [18F]FPHB were obtained in approx. 20-30% yields (EOS/EOB, decay corrected). Specific activities of 900-1700 Ci/mmol for [18F]FPHB and 800-1400 Ci/mmol for [18F]FPMB were obtained by reverse phase HPLC purification. Total synthesis and purification time required for either [18F]FPHB or [18F]FPMB was 120 min from EOB.
报道了一种含氟苯甲酰胺类抗精神病药物（S）-N-[(1-乙基-2-吡咯烷基)甲基]-5-(3-氟丙基)-2,3-二甲氧基苯甲酰胺的合成，该合成以3-(3,4-二甲氧基苯基)-1-丙醇为起始原料，总产率为20-25%。通过（S）-N-[(1-乙基-2-吡咯烷基)甲基-5-(3-甲苯磺酰氧基丙基)-2-甲氧基苯甲酰胺和（S）-N-[(1-乙基-2-吡咯烷基)甲基]-5-(3-甲苯磺酰氧基丙基)-2,3-二甲氧基苯甲酰胺分别与无载体添加的[18F]氟化物进行亲核取代反应，开展了（S）-N-[(1-乙基-2-吡咯烷基)甲基]-5-(3-[18F]氟丙基)-2-甲氧基苯甲酰胺（[18F]FPHB）和（S）-N-[(1-乙基-2-吡咯烷基)甲基]-5-(3-[18F]氟丙基)-2,3-二甲氧基苯甲酰胺（[18F]FPHB）的放射性合成。[18F]FPHB和[18F]FPHB的产率均约为20-30%（EOS/EOB，已校正衰变）。通过反相高效液相色谱纯化，[18F]FPHB的比活度为900-1700 Ci/mmol，[18F]FPMB的比活度为800-1400 Ci/mmol。从EOB开始，[18F]FPHB或[18F]FPMB所需的全合成和纯化时间为120分钟。
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