A concise total synthesis of largazole, solution structure, and some preliminary structure activity relationships

Org Lett. 2008 Aug 21;10(16):3595-8. doi: 10.1021/ol8013478. Epub 2008 Jul 11.

Abstract

A total synthesis of largazole that proceeds in 8 steps from commercial materials is reported, along with some structure-activity relationships. A combination of NMR studies and molecular modeling have also provided a preliminary picture of the conformation of largazole.

Publication types

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

MeSH terms

  • Animals
  • Cell Line, Tumor
  • Cell Proliferation / drug effects
  • Computer Simulation
  • Depsipeptides / chemical synthesis*
  • Depsipeptides / chemistry
  • Depsipeptides / pharmacology
  • Dose-Response Relationship, Drug
  • Drug Screening Assays, Antitumor
  • Humans
  • Magnetic Resonance Spectroscopy / methods
  • Mice
  • Models, Molecular
  • Molecular Structure
  • Monte Carlo Method
  • Solutions / chemistry
  • Structure-Activity Relationship
  • Thiazoles / chemical synthesis*
  • Thiazoles / chemistry
  • Thiazoles / pharmacology

Substances

  • Depsipeptides
  • Solutions
  • Thiazoles
  • largazole