Synthesis and biological evaluation of 1,7,8,8a-tetrahydro-3H-oxazolo[3,4-a]pyrazin-6(5H)-ones as antitumoral agents

Bioorg Med Chem. 2013 Sep 15;21(18):5748-53. doi: 10.1016/j.bmc.2013.07.019. Epub 2013 Jul 18.

Abstract

A series of 1,7,8,8a-tetrahydro-3H-oxazolo[3,4-a]pyrazin-6(5H)-ones has been synthesized by an intramolecular, palladium(II) catalyzed, aminooxygenation of alkenyl ureas, readily available from glycine allylamides as starting materials. Biological tests showed that the obtained compounds are endowed with an interesting antitumoral activity against two human thyroid cancer cell lines, namely FTC-133 and 8305C, by promoting the apoptotic pathway and DNA fragmentation.

Keywords: Bicyclic piperazinones; Caspase-3; Domino reaction; Palladium; Thyroid cancers.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antineoplastic Agents / chemical synthesis*
  • Antineoplastic Agents / chemistry
  • Antineoplastic Agents / toxicity
  • Apoptosis / drug effects
  • Caspase 3 / metabolism
  • Cell Line, Tumor
  • DNA Fragmentation / drug effects
  • Humans
  • Oxazoles / chemistry*
  • Pyrazines / chemical synthesis
  • Pyrazines / chemistry*
  • Pyrazines / toxicity
  • Structure-Activity Relationship

Substances

  • Antineoplastic Agents
  • Oxazoles
  • Pyrazines
  • Caspase 3