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

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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 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 μ-calpain inhibitory activities with IC50 values of 20.15 and 25.77 M, respectively.

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Authors and Affiliations

  1. College of Pharmacy, Yeungnam University, Gyeongsan, 712-749, Korea

    Jing Lu Liang, Hyo Chang Cha, Seung Ho Lee, Jong-Keun Son, Hyeun Wook Chang & Yurngdong Jahng

  2. College of Pharmacy & Division of Life & Pharmaceutical Sciences, Ewha Womans University, Seoul, 120-750, Korea

    Ji-Eun Eom & Youngjoo Kwon

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  1. Jing Lu Liang
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Liang, J.L., Cha, H.C., Lee, S.H. et al. A facile synthesis of emodin derivatives, emodin carbaldehyde, citreorosein, and their 10-deoxygenated derivatives and their inhibitory activities on μ-calpain. Arch. Pharm. Res. 35, 447–454 (2012). https://doi.org/10.1007/s12272-012-0307-4

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