Synthesis of (Z)-2-((1H-indazol-3-yl)methylene)-6-[11C]methoxy- 7-(piperazin-1-ylmethyl)benzofuran-3(2H)-one as a new potential PET probe for imaging of the enzyme PIM1

Mingzhang Gao, Min Wang, Kathy Miller, Qi-Huang Zheng

Research output: Contribution to journalArticle

9 Citations (Scopus)

Abstract

(Z)-2-((1H-Indazol-3-yl)methylene)-6-methoxy-7-(piperazin-1-ylmethyl) benzofuran-3(2H)-one is a potent and selective proviral integration site in moloney murine leukemia virus kinase 1 (PIM1) inhibitor with an IC50 value of 3 nM. (Z)-2-((1H-Indazol-3-yl)methylene)-6-[11C]methoxy-7- (piperazin-1-ylmethyl)benzofuran-3(2H)-one, a new potential PET probe for imaging of the enzyme PIM1, was first designed and synthesized in 20-30% decay corrected radiochemical yield and 370-740 GBq/μmol specific activity at end of bombardment (EOB). The synthetic strategy was to prepare a carbon-11-labeled Boc-protected intermediate followed by a quick acidic de-protection.

Original languageEnglish
Pages (from-to)4342-4346
Number of pages5
JournalBioorganic and Medicinal Chemistry Letters
Volume23
Issue number15
DOIs
StatePublished - Aug 1 2013

Fingerprint

Moloney murine leukemia virus
Imaging techniques
Enzymes
Viruses
Inhibitory Concentration 50
Phosphotransferases
Carbon
benzofuran
1-benzofuran

Keywords

  • (Z)-2-((1H-Indazol-3-yl)methylene)-6-[C]methoxy-7-(piperazin- 1-ylmethyl)benzofuran-3(2H)-one ([C]4)
  • Alzheimer's disease
  • Cancer
  • Positron emission tomography (PET)
  • Proviral integration site in moloney murine leukemia virus kinase 1 (PIM1)
  • Radiosynthesis

ASJC Scopus subject areas

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

Cite this

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title = "Synthesis of (Z)-2-((1H-indazol-3-yl)methylene)-6-[11C]methoxy- 7-(piperazin-1-ylmethyl)benzofuran-3(2H)-one as a new potential PET probe for imaging of the enzyme PIM1",
abstract = "(Z)-2-((1H-Indazol-3-yl)methylene)-6-methoxy-7-(piperazin-1-ylmethyl) benzofuran-3(2H)-one is a potent and selective proviral integration site in moloney murine leukemia virus kinase 1 (PIM1) inhibitor with an IC50 value of 3 nM. (Z)-2-((1H-Indazol-3-yl)methylene)-6-[11C]methoxy-7- (piperazin-1-ylmethyl)benzofuran-3(2H)-one, a new potential PET probe for imaging of the enzyme PIM1, was first designed and synthesized in 20-30{\%} decay corrected radiochemical yield and 370-740 GBq/μmol specific activity at end of bombardment (EOB). The synthetic strategy was to prepare a carbon-11-labeled Boc-protected intermediate followed by a quick acidic de-protection.",
keywords = "(Z)-2-((1H-Indazol-3-yl)methylene)-6-[C]methoxy-7-(piperazin- 1-ylmethyl)benzofuran-3(2H)-one ([C]4), Alzheimer's disease, Cancer, Positron emission tomography (PET), Proviral integration site in moloney murine leukemia virus kinase 1 (PIM1), Radiosynthesis",
author = "Mingzhang Gao and Min Wang and Kathy Miller and Qi-Huang Zheng",
year = "2013",
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language = "English",
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TY - JOUR

T1 - Synthesis of (Z)-2-((1H-indazol-3-yl)methylene)-6-[11C]methoxy- 7-(piperazin-1-ylmethyl)benzofuran-3(2H)-one as a new potential PET probe for imaging of the enzyme PIM1

AU - Gao, Mingzhang

AU - Wang, Min

AU - Miller, Kathy

AU - Zheng, Qi-Huang

PY - 2013/8/1

Y1 - 2013/8/1

N2 - (Z)-2-((1H-Indazol-3-yl)methylene)-6-methoxy-7-(piperazin-1-ylmethyl) benzofuran-3(2H)-one is a potent and selective proviral integration site in moloney murine leukemia virus kinase 1 (PIM1) inhibitor with an IC50 value of 3 nM. (Z)-2-((1H-Indazol-3-yl)methylene)-6-[11C]methoxy-7- (piperazin-1-ylmethyl)benzofuran-3(2H)-one, a new potential PET probe for imaging of the enzyme PIM1, was first designed and synthesized in 20-30% decay corrected radiochemical yield and 370-740 GBq/μmol specific activity at end of bombardment (EOB). The synthetic strategy was to prepare a carbon-11-labeled Boc-protected intermediate followed by a quick acidic de-protection.

AB - (Z)-2-((1H-Indazol-3-yl)methylene)-6-methoxy-7-(piperazin-1-ylmethyl) benzofuran-3(2H)-one is a potent and selective proviral integration site in moloney murine leukemia virus kinase 1 (PIM1) inhibitor with an IC50 value of 3 nM. (Z)-2-((1H-Indazol-3-yl)methylene)-6-[11C]methoxy-7- (piperazin-1-ylmethyl)benzofuran-3(2H)-one, a new potential PET probe for imaging of the enzyme PIM1, was first designed and synthesized in 20-30% decay corrected radiochemical yield and 370-740 GBq/μmol specific activity at end of bombardment (EOB). The synthetic strategy was to prepare a carbon-11-labeled Boc-protected intermediate followed by a quick acidic de-protection.

KW - (Z)-2-((1H-Indazol-3-yl)methylene)-6-[C]methoxy-7-(piperazin- 1-ylmethyl)benzofuran-3(2H)-one ([C]4)

KW - Alzheimer's disease

KW - Cancer

KW - Positron emission tomography (PET)

KW - Proviral integration site in moloney murine leukemia virus kinase 1 (PIM1)

KW - Radiosynthesis

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