Synthesis of 8-Methoxypenciclovir and 8-Methoxyganciclovir through Methyl Triflate, a New Potential Approach to Label Penciclovir and Ganciclovir with Carbon-11

Qi-Huang Zheng; Ji-Quan Wang; Xiangshu Fei; Gary D. Hutchins

doi:10.1055/s-2003-42454

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Synthesis 2003(18): 2785-2794
DOI: 10.1055/s-2003-42454

PAPER

Synthesis of 8-Methoxypenciclovir and 8-Methoxyganciclovir through Methyl Triflate, a New Potential Approach to Label Penciclovir and Ganciclovir with Carbon-11

Qi-Huang Zheng*, Ji-Quan Wang, Xiangshu Fei, Gary D. Hutchins
Department of Radiology, Indiana University School of Medicine, 1345 West 16th Street, L-3 Room 202, Indianapolis, IN 46202-2111, USA
Fax: +1(317)2789711; e-Mail: qzheng@iupui.edu;

Further Information

Publication History

Received 4 August 2003
Publication Date:
23 October 2003 (online)

Abstract
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Abstract

In an effort to make HSV-tk gene reporter probes 8-FPCV and 8-FGCV labeled with fluorine-18, via the nucleophilic substitution reaction of PCV and GCV quaternized methylamine salt precursors with KF/Kryptofix 2.2.2, a new and unusual reaction through methyl triflate was discovered. Subsequently, new compounds 8-MeOPCV and 8-MeOGCV were synthesized from PCV and GCV in six steps with 12% and 20% overall chemical yield, respectively, and a novel potential approach to label PCV and GCV with carbon-11 has been proposed.

Key words

gene reporter probes - herpes simplex virus thymidine kinase (HSV-tk) - positron emission tomography (PET) - 8-methoxypenciclovir - 8-methoxyganciclovir

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