A facile synthesis of emodin derivatives, emodin carbaldehyde, citreorosein, and their 10-deoxygenated derivatives and their inhibitory activities on μ-calpain

Arch Pharm Res. 2012 Mar;35(3):447-54. doi: 10.1007/s12272-012-0307-4. Epub 2012 Apr 5.

Abstract

A new procedure for the preparation of emodin carbaldehyde and citreorosein was described, in which, ω,ω'-dibromomethylemodin triacetate was prepared as a key intermediate by NBSmediated bromination of 1,3,8-triacetylemodin. Reduction of emodin and citreorosein with SnCl(2) in a 1:1 mixture of HOAc and HCl afforded the corresponding anthrones in 90% and 92% yield, respectively, while the corresponding 10-desoxyemodin carbaldehyde was prepared by MnO(2) oxidation of 10-desoxycitreorosein. 10-Desoxycitreorosein and emodin carbaldehyde showed feasible μ-calpain inhibitory activities with IC(50) values of 20.15 and 25.77 M, respectively.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Aldehydes / chemical synthesis*
  • Aldehydes / pharmacology*
  • Anthraquinones / chemical synthesis*
  • Anthraquinones / pharmacology*
  • Calpain / antagonists & inhibitors*
  • Cysteine Proteinase Inhibitors / chemical synthesis*
  • Cysteine Proteinase Inhibitors / pharmacology*
  • Emodin / analogs & derivatives
  • Emodin / chemical synthesis*
  • Emodin / pharmacology*
  • Fluorometry
  • Humans
  • Magnetic Resonance Spectroscopy
  • Molecular Structure
  • Oxidation-Reduction
  • Spectrophotometry, Infrared

Substances

  • Aldehydes
  • Anthraquinones
  • Cysteine Proteinase Inhibitors
  • Calpain
  • mu-calpain
  • Emodin
  • citreorosein