Rapid synthesis of F-18 and H-2 dual-labeled altanserin. A metabolically resistant PET ligand for 5-HT(2A) receptors

Ping Zhong Tan, Ronald M. Baldwin, Tao Fu, Dennis S. Charney, Robert B. Innis

Research output: Contribution to journalArticlepeer-review

31 Scopus citations

Abstract

F-18 and H-2 dual-labeled altanserin (3, [18F]d-ALT), a novel PET tracer for 5-HT(2A) receptors with metabolically resistant properties, was synthesized by [18F]fluoride displacement of the corresponding deuterated nitro precursor in 32% yield (EOB) in 108 min with radiochemical purity 95% and specific activity > 1000 mCi/μmol (EOS). The key intermediate ethyl N-(2-chloroethyl-2,2-d2)carbamate (7) was obtained by LiAID4 reduction of a glycine ester (93%), chlorination and carbamoylation (79%). 4-(4-Nitrobenzoyl)piperidine (13) was synthesized (60%) by improving the published coupling reaction of p-nitrophenyltrimethylstannane (10), obtained from p-iodonitrobenzene and (CH3)6Sn2 (94%), with 1-benzoylisonipecotic acid chloride (11) followed by acid hydrolysis. 13 was alkylated with 7 (82%), hydrolyzed and condensed with methyl o-isothiocyanatobenzoyate to provide with the precursor deuteronitroaltanserin (4, 75%).

Original languageEnglish
Pages (from-to)457-467
Number of pages11
JournalJournal of Labelled Compounds and Radiopharmaceuticals
Volume42
Issue number5
DOIs
StatePublished - 1999
Externally publishedYes

Keywords

  • 5-HT
  • Deuterium isotope effect
  • PET
  • Receptor
  • [F]altanserin

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