Synthesis of highly substituted dibenzo[b,f]azocines and their evaluation as protein kinase inhibitors

Bioorg Med Chem Lett. 2006 Oct 15;16(20):5360-3. doi: 10.1016/j.bmcl.2006.07.078. Epub 2006 Aug 4.

Abstract

Synthetic routes towards highly substituted eight membered ring heterocycles fused to aryl rings such as the dibenzo[b,f]azocine system are still lacking. Herein, we present a convenient convergent synthetic route towards this heterocyclic class of compounds with possible variations at positions 4, 7, and 11. One member of a library of dibenzo[b,f]azocines with different substituents at position 11 was identified to inhibit protein kinase A activity (IC(50)=122microM) but not protein kinase C.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Azocines / chemical synthesis*
  • Azocines / chemistry
  • Azocines / pharmacology*
  • Drug Evaluation, Preclinical
  • Enzyme Activation / drug effects
  • Molecular Structure
  • Protein Kinase Inhibitors / chemical synthesis*
  • Protein Kinase Inhibitors / chemistry
  • Protein Kinase Inhibitors / pharmacology*
  • Protein Kinases / drug effects*
  • Stereoisomerism
  • Structure-Activity Relationship
  • Substrate Specificity

Substances

  • Azocines
  • Protein Kinase Inhibitors
  • Protein Kinases