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

Jing Lu Liang, Hyo Chang Cha, Seung Ho Lee, Jong Keun Son, Hyeun Wook Chang, Ji Eun Eom, Youngjoo Kwon, Yurngdong Jahng

Research output: Contribution to journalArticlepeer-review

8 Scopus citations

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.

Original languageEnglish
Pages (from-to)447-454
Number of pages8
JournalArchives of Pharmacal Research
Volume35
Issue number3
DOIs
StatePublished - Mar 2012

Bibliographical note

Funding Information:
Financial support from Yeungnam University Research Grant (2008) is gratefully appreciated.

Keywords

  • Anthrone
  • Citreorosein
  • Emodin
  • Emodin carbaldehyde
  • μ-Calpain
  • ω
  • ω'- Dibromomethylemodin

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