A facile synthesis of emodin derivatives, emodin carbaldehyde, citreorosein, and their 10-deoxygenated derivatives and their inhibitory activities on μ-calpain
| Autor: | Yurngdong Jahng, Hyeun Wook Chang, Youngjoo Kwon, Jing Lu Liang, Seung Ho Lee, Hyo Chang Cha, Jong-Keun Son, Ji-Eun Eom |
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| Rok vydání: | 2011 |
| Předmět: |
Emodin
Magnetic Resonance Spectroscopy Spectrophotometry Infrared Anthraquinones Cysteine Proteinase Inhibitors Inhibitory postsynaptic potential Medicinal chemistry chemistry.chemical_compound Drug Discovery Ic50 values Humans Fluorometry Aldehydes Citreorosein biology Molecular Structure Chemistry Calpain Organic Chemistry Halogenation Yield (chemistry) biology.protein Molecular Medicine Oxidation-Reduction |
| Zdroj: | Archives of pharmacal research. 35(3) |
| ISSN: | 1976-3786 |
| Popis: | 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. |
| Databáze: | OpenAIRE |
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