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

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

doi:10.1007/s12272-012-0307-4

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

Jing Lu Liang, Hyo Chang Cha, Seung Ho Lee, Jong Keun Son, Hyeun Wook Chang, Ji Eun Eom, Youngjoo Kwon, Yurngdong Jahng

Department of Pharmaceutical Sciences

Research output: Contribution to journal › Article › peer-review

9 Scopus citations

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.

Original language	English
Pages (from-to)	447-454
Number of pages	8
Journal	Archives of Pharmacal Research
Volume	35
Issue number	3
DOIs	https://doi.org/10.1007/s12272-012-0307-4
State	Published - Mar 2012

Bibliographical note

Funding Information:
Financial support from Yeungnam University Research Grant (2008) is gratefully appreciated.

Keywords

Anthrone
Citreorosein
Emodin
Emodin carbaldehyde
μ-Calpain
ω
ω'- Dibromomethylemodin

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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.",

keywords = "Anthrone, Citreorosein, Emodin, Emodin carbaldehyde, μ-Calpain, ω, ω'- Dibromomethylemodin",

author = "Liang, {Jing Lu} and Cha, {Hyo Chang} and Lee, {Seung Ho} and Son, {Jong Keun} and Chang, {Hyeun Wook} and Eom, {Ji Eun} and Youngjoo Kwon and Yurngdong Jahng",

note = "Funding Information: Financial support from Yeungnam University Research Grant (2008) is gratefully appreciated.",

year = "2012",

month = mar,

doi = "10.1007/s12272-012-0307-4",

language = "English",

volume = "35",

pages = "447--454",

journal = "Archives of Pharmacal Research",

issn = "0253-6269",

publisher = "Pharmaceutical Society of Korea",

number = "3",

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TY - JOUR

T1 - A facile synthesis of emodin derivatives, emodin carbaldehyde, citreorosein, and their 10-deoxygenated derivatives and their inhibitory activities on μ-calpain

AU - Liang, Jing Lu

AU - Cha, Hyo Chang

AU - Lee, Seung Ho

AU - Son, Jong Keun

AU - Chang, Hyeun Wook

AU - Eom, Ji Eun

AU - Kwon, Youngjoo

AU - Jahng, Yurngdong

N1 - Funding Information: Financial support from Yeungnam University Research Grant (2008) is gratefully appreciated.

PY - 2012/3

Y1 - 2012/3

N2 - 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.

AB - 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.

KW - Anthrone

KW - Citreorosein

KW - Emodin

KW - Emodin carbaldehyde

KW - μ-Calpain

KW - ω

KW - ω'- Dibromomethylemodin

UR - http://www.scopus.com/inward/record.url?scp=84862904293&partnerID=8YFLogxK

U2 - 10.1007/s12272-012-0307-4

DO - 10.1007/s12272-012-0307-4

M3 - Article

C2 - 22477191

AN - SCOPUS:84862904293

SN - 0253-6269

VL - 35

SP - 447

EP - 454

JO - Archives of Pharmacal Research

JF - Archives of Pharmacal Research

IS - 3

ER -

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

Abstract

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Keywords

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