Synthesis and Evaluation of Three Structurally Related 18F-Labeled Orvinols of Different Intrinsic Activities: 6-O-[18F]Fluoroethyl-diprenorphine ([18F]FDPN), 6-O-[18F]Fluoroethyl-buprenorphine ([18F]FBPN), and 6-O-[18F]Fluoroethyl-phenethyl-orvinol ([18F]FPEO)

被引：15
|
作者：
Schoultz, Bent W. [1 ]
Hjornevik, Trine [2 ,3 ]
Reed, Brian J. [1 ,2 ]
Marton, Janos [4 ]
Coello, Christopher S. [2 ]
Willoch, Frode [2 ,5 ]
Henriksen, Gjermund [2 ,6 ]
机构：
[1] Univ Oslo, Dept Chem, N-0315 Oslo, Norway
[2] Univ Oslo, Inst Basic Med Sci, N-0317 Oslo, Norway
[3] Oslo Univ Hosp, Intervent Ctr, Oslo, Norway
[4] Biomed Forsch Reagenzien GmbH, ABX Adv Biochem Cpds, D-01454 Radeberg, Germany
[5] Aleris AS, N-0264 Oslo, Norway
[6] Norwegian Med Cyclotron Ctr, N-0424 Oslo, Norway
来源：
JOURNAL OF MEDICINAL CHEMISTRY | 2014年 / 57卷 / 12期
关键词：
BUPRENORPHINE; RECEPTOR; ORIPAVINE; AGONIST;
D O I：
10.1021/jm500503k
中图分类号：
R914 [药物化学];
学科分类号：
100701 ;
摘要：
We report the synthesis and biological evaluation of a triplet of 6-O-F-18-fluoroethylated derivatives of structurally related orvinols that span across the full range of intrinsic activities, the antagonist diprenorphine, the partial agonist buprenorphine, and the full agonist phenethyl-orvinol. [F-18]fluoroethyl-diprenorphine, [F-18]fluoroethyl-buprenorphine, and [F-18]fluoroethyl-phenethyl-orvinol were prepared in high yields and quality from their 6-O-desmethyl-precursors. The results indicate suitable properties of the three 6-O-F-18-fluoroethylated derivatives as functional analogues to the native carbon-11 labeled versions with similar pharmacological properties.
引用
收藏
页码：5464 / 5469
页数：6
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