Synthesis and evaluation of pyridylbenzofuran, pyridylbenzothiazole and pyridylbenzoxazole derivatives as ¹⁸F-PET imaging agents for β-amyloid plaques

Bioorg Med Chem Lett. 2012 Jul 1;22(13):4332-7. doi: 10.1016/j.bmcl.2012.05.011. Epub 2012 May 11.

Abstract

The synthesis and SAR of new β-amyloid binding agents are reported. Evaluation of important properties for achieving good signal-to-background ratio is described. Compounds 27, 33, and 36 displayed desirable lipophilic and pharmacokinetic properties. Compound 27 was further evaluated with autoradiographic studies in vitro on human brain tissue and in vivo in Tg2576 mice. Compound 27 showed an increased signal-to-background ratio compared to flutemetamol 4, indicating its suitability as PET ligand for β-amyloid deposits in AD patients. The preparation of the corresponding (18)F-labeled PET radioligand of compound 27 is presented.

MeSH terms

  • Alzheimer Disease / diagnosis
  • Aminopyridines / chemical synthesis*
  • Aminopyridines / pharmacokinetics
  • Amyloid beta-Peptides / chemistry*
  • Amyloid beta-Peptides / metabolism
  • Animals
  • Benzofurans / chemical synthesis
  • Benzofurans / chemistry*
  • Benzofurans / pharmacokinetics
  • Benzothiazoles / chemistry*
  • Benzothiazoles / pharmacokinetics
  • Benzoxazoles / chemistry*
  • Benzoxazoles / pharmacokinetics
  • Brain / metabolism
  • Contrast Media / chemical synthesis*
  • Contrast Media / pharmacokinetics
  • Fluorine Radioisotopes / chemistry
  • Humans
  • Mice
  • Mice, Transgenic
  • Positron-Emission Tomography
  • Radiopharmaceuticals / chemical synthesis*
  • Radiopharmaceuticals / pharmacokinetics
  • Structure-Activity Relationship

Substances

  • Aminopyridines
  • Amyloid beta-Peptides
  • Benzofurans
  • Benzothiazoles
  • Benzoxazoles
  • Contrast Media
  • Fluorine Radioisotopes
  • Radiopharmaceuticals
  • benzothiazole