Synthesis of carbon-11-labeled 4-(phenylamino)-pyrrolo[2,1-f][1,2,4] triazine derivatives as new potential PET tracers for imaging of p38α mitogen-activated protein kinase

Min Wang, Mingzhang Gao, Qi Huang Zheng

Research output: Contribution to journalArticle

6 Scopus citations

Abstract

The reference standards methyl 4-(2-methyl-5-(methoxycarbamoyl)phenylamino) -5-methylpyrrolo[2,1-f][1,2,4]triazine-6-carboxylate (10a), methyl 4-(2-methyl-5-(ethoxycarbamoyl)phenylamino)-5-methylpyrrolo[2,1-f][1,2,4] triazine-6-carboxylate (10b) and corresponding precursors 4-(2-methyl-5- (methoxycarbamoyl)phenylamino)-5-methylpyrrolo[2,1-f][1,2,4]triazine-6- carboxylic acid (11a), methyl 4-(2-methyl-5-(ethoxycarbamoyl)phenylamino)-5- methylpyrrolo[2,1-f][1,2,4]triazine-6-carboxylic acid (11b) were synthesized from methyl crotonate and 3-amino-4-methylbenzoic acid in multiple steps with moderate to excellent yields. The target tracer [11C]methyl 4-(2-methyl-5-(methoxycarbamoyl)phenylamino)-5-methylpyrrolo[2,1-f][1,2,4] triazine-6-carboxylate ([11C]10a) and [11C]methyl 4-(2-methyl-5-(ethoxycarbamoyl)phenylamino)-5-methylpyrrolo[2,1-f][1,2,4] triazine-6-carboxylate ([11C]10b) were prepared from their corresponding precursors with [11C]CH3OTf under basic condition through O-[11C]methylation and isolated by a simplified solid-phase extraction (SPE) method in 50-60% radiochemical yields at end of bombardment (EOB) with 185-555 GBq/μmol specific activity at end of synthesis (EOS).

Original languageEnglish (US)
Pages (from-to)3700-3705
Number of pages6
JournalBioorganic and Medicinal Chemistry Letters
Volume24
Issue number16
DOIs
StatePublished - Aug 15 2014

Keywords

  • Cancer
  • Carbon-11-labeled 4-(phenylamino)-pyrrolo[2,1-f][1,2,4]triazine derivatives
  • Diabetes
  • Inflammation
  • p38α mitogen-activated protein kinase (MAPK)
  • Positron emission tomography (PET)

ASJC Scopus subject areas

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

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