Substituted furo[3,2-b]pyridines: novel bioisosteres of 5-HT 1F receptor agonists

Bioorg Med Chem Lett. 2004 Jan 5;14(1):167-70. doi: 10.1016/j.bmcl.2003.09.091.


Synthesis and evaluation of a series of 2,3,5- and 3,5-substituted furo[3,2-b]pyridines were undertaken in order to investigate their utility as bioisosteres of 5-HT(1F) receptor agonist indole analogues, 1-3. The replacement proved to be effective, providing compounds with similar 5-HT(1F) receptor affinity and improved selectivity when compared with the indole analogues. Through these studies we identified 4-fluoro-N-[3-(1-methyl-piperidin-4-yl)-furo[3,2-b]pyridin-5-yl]-benzamide (5), a potent and selective 5-HT(1F) receptor agonist with the potential to treat acute migraine.

Publication types

  • Comparative Study

MeSH terms

  • Protein Binding / physiology
  • Pyridines / chemistry*
  • Pyridines / metabolism*
  • Receptors, Serotonin / metabolism*
  • Serotonin Receptor Agonists / chemistry*
  • Serotonin Receptor Agonists / metabolism*


  • Pyridines
  • Receptors, Serotonin
  • Serotonin Receptor Agonists
  • serotonin 1F receptor