Synthesis of carbon-11-labeled aminoalkylindole derivatives as new candidates of cannabinoid receptor radioligands for PET imaging of alcohol abuse

Mingzhang Gao, Andy Chufan Gao, Min Wang, Qi-Huang Zheng

Research output: Contribution to journalArticle

3 Citations (Scopus)

Abstract

Carbon-11-labeled aminoalkylindole derivatives (1-butyl-7-[<sup>11</sup>C]methoxy-1H-indol-3-yl)(naphthalene-1-yl)methanone ([<sup>11</sup>C]3), 1-butyl-7-[<sup>11</sup>C]methoxy-3-(naphthalene-1-ylmethyl)-1H-indole ([<sup>11</sup>C]5), and 1-butyl-7-[<sup>11</sup>C]methoxy-3-(naphthalene-2-yl)-1H-indole ([<sup>11</sup>C]8) were prepared by O-[<sup>11</sup>C]methylation of their corresponding precursors with [<sup>11</sup>C]CH<inf>3</inf>OTf under basic condition (2 N NaOH) and isolated by a simplified solid-phase extraction (SPE) method in 50-60% radiochemical yields based on [<sup>11</sup>C]CO<inf>2</inf> and decay corrected to end of bombardment (EOB). The overall synthesis time from EOB was 23 min, the radiochemical purity was >99%, and the specific activity at end of synthesis (EOS) was 185-555 GBq/μmol.

Original languageEnglish
Pages (from-to)5581-5586
Number of pages6
JournalBioorganic and Medicinal Chemistry Letters
Volume24
Issue number24
DOIs
StatePublished - Dec 15 2014

Fingerprint

Cannabinoid Receptors
Alcoholism
Carbon
Alcohols
Derivatives
Imaging techniques
Methylation
Solid Phase Extraction
naphthalene
indole

Keywords

  • Alcohol abuse
  • Cannabinoid receptor
  • Carbon-11-labeled aminoalkylindole
  • derivatives
  • Positron emission tomography (PET)
  • Radiosynthesis

ASJC Scopus subject areas

  • Biochemistry
  • Clinical Biochemistry
  • Molecular Biology
  • Molecular Medicine
  • Organic Chemistry
  • Drug Discovery
  • Pharmaceutical Science
  • Medicine(all)

Cite this

Synthesis of carbon-11-labeled aminoalkylindole derivatives as new candidates of cannabinoid receptor radioligands for PET imaging of alcohol abuse. / Gao, Mingzhang; Gao, Andy Chufan; Wang, Min; Zheng, Qi-Huang.

In: Bioorganic and Medicinal Chemistry Letters, Vol. 24, No. 24, 15.12.2014, p. 5581-5586.

Research output: Contribution to journalArticle

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