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 Hutchins

Research output: Contribution to journalArticle

11 Citations (Scopus)

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.

Original languageEnglish
Pages (from-to)2785-2794
Number of pages10
JournalSynthesis
Issue number18
StatePublished - 2003

Fingerprint

Ganciclovir
Fluorine
Labels
Substitution reactions
Carbon
Salts
Genes
penciclovir
methyl triflate
methylamine

Keywords

  • 8-methoxyganciclovir
  • 8-methoxypenciclovir
  • Gene reporter probes
  • Herpes simplex virus thymidine kinase (HSV-tk)
  • Positron emission tomography (PET)

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

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title = "Synthesis of 8-Methoxypenciclovir and 8-Methoxyganciclovir through Methyl Triflate, a New Potential Approach to Label Penciclovir and Ganciclovir with Carbon-11",
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.",
keywords = "8-methoxyganciclovir, 8-methoxypenciclovir, Gene reporter probes, Herpes simplex virus thymidine kinase (HSV-tk), Positron emission tomography (PET)",
author = "Qi-Huang Zheng and Wang, {Ji Quan} and Xiangshu Fei and Gary Hutchins",
year = "2003",
language = "English",
pages = "2785--2794",
journal = "Synthesis",
issn = "0039-7881",
publisher = "Georg Thieme Verlag",
number = "18",

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TY - JOUR

T1 - Synthesis of 8-Methoxypenciclovir and 8-Methoxyganciclovir through Methyl Triflate, a New Potential Approach to Label Penciclovir and Ganciclovir with Carbon-11

AU - Zheng, Qi-Huang

AU - Wang, Ji Quan

AU - Fei, Xiangshu

AU - Hutchins, Gary

PY - 2003

Y1 - 2003

N2 - 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.

AB - 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.

KW - 8-methoxyganciclovir

KW - 8-methoxypenciclovir

KW - Gene reporter probes

KW - Herpes simplex virus thymidine kinase (HSV-tk)

KW - Positron emission tomography (PET)

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SP - 2785

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