title: A facile synthesis of emodin derivatives, emodin carbaldehyde, citreorosein, and their 10-deoxygenated derivatives and their inhibitory activities on μ-calpain.
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.
authors.affiliation: College of Pharmacy, Yeungnam University, Gyeongsan 712-749, Korea.
authors.forename: Jing Lu
authors.initials: JL
authors.lastname: Liang
authors.forename: Hyo Chang
authors.initials: HC
authors.lastname: Cha
authors.forename: Seung Ho
authors.initials: SH
authors.lastname: Lee
authors.forename: Jong-Keun
authors.initials: JK
authors.lastname: Son
authors.forename: Hyeun Wook
authors.initials: HW
authors.lastname: Chang
authors.forename: Ji-Eun
authors.initials: JE
authors.lastname: Eom
authors.forename: Youngjoo
authors.initials: Y
authors.lastname: Kwon
authors.forename: Yurngdong
authors.initials: Y
authors.lastname: Jahng
mesh_terms: D000447:Aldehydes / Q000138:chemical synthesis* / Q000494:pharmacology*; D000880:Anthraquinones / Q000138:chemical synthesis* / Q000494:pharmacology*; D002154:Calpain / Q000037:antagonists & inhibitors*; D015853:Cysteine Proteinase Inhibitors / Q000138:chemical synthesis* / Q000494:pharmacology*; D004642:Emodin / Q000031:analogs & derivatives / Q000138:chemical synthesis* / Q000494:pharmacology*; D005470:Fluorometry; D006801:Humans; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D010084:Oxidation-Reduction; D013055:Spectrophotometry, Infrared
chemical_list: D000447:Aldehydes; D000880:Anthraquinones; D015853:Cysteine Proteinase Inhibitors; D002154:Calpain; C449002:mu-calpain; D004642:Emodin; C540595:citreorosein