Synthesis and solid-phase purification of anthranilic sulfonamides as CCK-2 ligands

Bioorg Med Chem Lett. 2007 Dec 15;17(24):6905-9. doi: 10.1016/j.bmcl.2007.09.087. Epub 2007 Sep 29.

Abstract

A novel strategy for the synthesis of cholecystokinin-2 receptor ligands was developed. The route employs a solution-phase synthesis of a series of anthranilic sulfonamides followed by a resin capture purification strategy to produce multi-milligram quantities of compounds for bioassay. The synthesis was used to produce >100 compounds containing various functional groups, highlighting the general applicability of this strategy and to address specific metabolism issues in our CCK-2 program.

MeSH terms

  • Animals
  • Cholecystokinin / metabolism*
  • Combinatorial Chemistry Techniques*
  • Drug Design
  • Humans
  • Ligands
  • Microsomes, Liver / drug effects
  • Molecular Structure
  • Rats
  • Receptor, Cholecystokinin B / metabolism*
  • Structure-Activity Relationship
  • Sulfonamides / chemical synthesis*
  • Sulfonamides / chemistry
  • Sulfonamides / pharmacology*
  • ortho-Aminobenzoates / chemical synthesis*
  • ortho-Aminobenzoates / chemistry
  • ortho-Aminobenzoates / pharmacology*

Substances

  • Ligands
  • Receptor, Cholecystokinin B
  • Sulfonamides
  • ortho-Aminobenzoates
  • Cholecystokinin