A Facile Synthesis of Emodin Derivatives, Emodin Carbaldehyde, Citreorosein, and Their 10-Deoxygenated Derivatives and Their Inhibitory Activities on mu-Calpain

作者：Liang Jing Lu; Cha Hyo Chang; Lee Seung Ho; Son Jong Keun; Chang Hyeun Wook; Eom Ji Eun; Kwon Youngjoo; Jahng Yurngdong^*

来源：Archives of Pharmacal Research, 2012, 35(3): 447-454.

DOI：10.1007/s12272-012-0307-4

• Emodin
• Emodin carbaldehyde
• Citreorosein
• omega,omega %26apos
• -Dibromomethylemodin
• mu-Calpain
• Anthrone

A new procedure for the preparation of emodin carbaldehyde and citreorosein was described, in which, omega,omega%26apos;-dibromomethylemodin triacetate was prepared as a key intermediate by NBS-mediated bromination of 1,3,8-triacetylemodin. Reduction of emodin and citreorosein with SnCl2 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 MnO2 oxidation of 10-desoxycitreorosein. 10-Desoxycitreorosein and emodin carbaldehyde showed feasible mu-calpain inhibitory activities with IC50 values of 20.15 and 25.77 M, respectively.

• 出版日期2012-3