Synthesis of carbon-11 and fluorine-18 labeled N-acetyl-1-aryl-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline derivatives as new potential PET AMPA receptor ligands

Bioorg Med Chem Lett. 2006 Apr 15;16(8):2229-33. doi: 10.1016/j.bmcl.2006.01.042. Epub 2006 Feb 7.

Abstract

New carbon-11 and fluorine-18 labeled N-acetyl-1-aryl-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline derivatives were designed and synthesized as potential positron emission tomography AMPA (2-amino-3-(3-hydroxy-5-methylisoxazol-4-yl)propionic acid) receptor ligands to image brain diseases. The single crystal structure of the most potent compound N-acetyl-1-(4'-chlorophenyl)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline (5a) is first reported.

Publication types

  • Research Support, Non-U.S. Gov't
  • Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

  • Amides / chemical synthesis
  • Amides / pharmacology*
  • Animals
  • Anticonvulsants / chemical synthesis*
  • Anticonvulsants / pharmacology
  • Anticonvulsants / therapeutic use
  • Carbon / chemistry
  • Fluorine / chemistry
  • Isoquinolines / chemical synthesis
  • Isoquinolines / pharmacology*
  • Isoquinolines / therapeutic use
  • Isotope Labeling
  • Ligands
  • Mice
  • Molecular Structure
  • Positron-Emission Tomography
  • Receptors, AMPA / antagonists & inhibitors*
  • Seizures / drug therapy

Substances

  • Amides
  • Anticonvulsants
  • Isoquinolines
  • Ligands
  • R-4-(3-hydroxyphenyl)-N,N-7,8-tetramethyl-3,4-dihydroisoquinoline-2(1H)-carboxamide
  • Receptors, AMPA
  • Fluorine
  • Carbon