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KMID : 0043320120350030447
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Archives of Pharmacal Research
2012 Volume.35 No. 3 p.447 ~ p.454
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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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Liang Jing Lu
Cha Hyo-Chang
Lee Seung-Ho
Son Jong-Keun
Chang Hyeun-Wook
Eom Ji-Eun
Kwon Young-Joo
Jahng Yurngdong
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Abstract
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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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KEYWORD
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Emodin, Emodin carbaldehyde, Citreorosein, ω, ω′-Dibromomethylemodin, μ-Calpain, Anthrone
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