Novel CGRP receptor antagonists through a design strategy of target simplification with addition of molecular flexibility

Bioorg Med Chem Lett. 2009 Oct 1;19(19):5787-90. doi: 10.1016/j.bmcl.2009.07.134. Epub 2009 Aug 6.

Abstract

A novel class of CGRP receptor antagonists was rationally designed by modifying a highly potent, but structurally complex, CGRP receptor antagonist. Initial modifications focused on simplified structures, with increased flexibility. Subsequent to the preparation of a less-potent but more flexible lead, classic medicinal chemistry methods were applied to restore high affinity (compound 22, CGRP Ki=0.035 nM) while maintaining structural diversity relative to the lead. Good selectivity against the closely related adrenomedullin-2 receptor was also achieved.

MeSH terms

  • Acetamides / chemical synthesis
  • Acetamides / chemistry*
  • Acetamides / pharmacology
  • Animals
  • Calcitonin Gene-Related Peptide Receptor Antagonists*
  • Cell Line
  • Drug Design
  • Humans
  • Rats
  • Receptors, Calcitonin Gene-Related Peptide / metabolism
  • Spiro Compounds / chemical synthesis
  • Spiro Compounds / chemistry*
  • Spiro Compounds / pharmacology
  • Structure-Activity Relationship

Substances

  • Acetamides
  • Calcitonin Gene-Related Peptide Receptor Antagonists
  • Receptors, Calcitonin Gene-Related Peptide
  • Spiro Compounds