CN

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

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

Bioorganic & medicinal chemistry letters (2014-12-04)

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

ABSTRACT

Carbon-11-labeled aminoalkylindole derivatives (1-butyl-7-[(11)C]methoxy-1H-indol-3-yl)(naphthalene-1-yl)methanone ([(11)C]3), 1-butyl-7-[(11)C]methoxy-3-(naphthalene-1-ylmethyl)-1H-indole ([(11)C]5), and 1-butyl-7-[(11)C]methoxy-3-(naphthalene-2-yl)-1H-indole ([(11)C]8) were prepared by O-[(11)C]methylation of their corresponding precursors with [(11)C]CH3OTf under basic condition (2N NaOH) and isolated by a simplified solid-phase extraction (SPE) method in 50-60% radiochemical yields based on [(11)C]CO2 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.

MATERIALS

Product Number

Brand

Product Description

Sigma-Aldrich

1,3-Propylene sulfite, 99%

Sigma-Aldrich

Methanol solution, contains 0.50 % (v/v) triethylamine

Sigma-Aldrich

Methanol solution, NMR reference standard, 4% in methanol-d₄ (99.8 atom % D), NMR tube size 3 mm × 8 in.

Supelco

Residual Solvent - Acetonitrile, Pharmaceutical Secondary Standard; Certified Reference Material

Supelco

Acetonitrile, analytical standard

Sigma-Aldrich

Acetonitrile, anhydrous, 99.8%

Supelco

Methanol, analytical standard

Sigma-Aldrich

Methanol-¹²C, 99.95 atom % ¹²C

Sigma-Aldrich

Methanol, NMR reference standard

Sigma-Aldrich

Acetonitrile, Preparateur, ≥99.9% (GC), One-time steel-plastic (SP) drum

Sigma-Aldrich

Methanol, purification grade, 99.8%

Sigma-Aldrich

Methanol, HPLC Plus, ≥99.9%

Sigma-Aldrich

Methanol, suitable for HPLC, gradient grade, suitable as ACS-grade LC reagent, ≥99.9%

Sigma-Aldrich

Acetonitrile, suitable for HPLC, gradient grade, ≥99.9%

Sigma-Aldrich

Acetonitrile, suitable for HPLC-GC, ≥99.8% (GC)

Sigma-Aldrich

Methanol, suitable for HPLC, gradient grade, ≥99.9%

Sigma-Aldrich

Acetonitrile, for HPLC, for UV, ≥99.9% (GC)

Sigma-Aldrich

Methanol, suitable for HPLC, ≥99.9%

Sigma-Aldrich

Acetonitrile, suitable for HPLC, gradient grade, ≥99.9%

Supelco

Methanol, Pharmaceutical Secondary Standard; Certified Reference Material

Sigma-Aldrich

Acetonitrile, suitable for DNA synthesis, ≥99.9% (GC)

Sigma-Aldrich

Methanol, puriss., meets analytical specification of Ph Eur, ≥99.7% (GC)

Sigma-Aldrich

Acetonitrile, biotech. grade, ≥99.93%

Sigma-Aldrich

Acetonitrile, ≥99.5% (GC)

Sigma-Aldrich

Acetonitrile, ACS reagent, ≥99.5%

Sigma-Aldrich

Methanol, BioReagent, ≥99.93%

Sigma-Aldrich

Methanol, ACS reagent, ≥99.8%

Sigma-Aldrich

Methanol, puriss. p.a., ACS reagent, reag. ISO, reag. Ph. Eur., ≥99.8% (GC)

USP

Residual Solvent Class 2 - Acetonitrile, United States Pharmacopeia (USP) Reference Standard

Supelco

Acetonitrile, Pharmaceutical Secondary Standard; Certified Reference Material