Efficient synthesis of 2,3-dimethoxy-5-methyl-6-morpholinomethyl-1,4-benzoquinone hydrochloride

被引:3
作者
Wang, Jin [1 ]
Liao, Teng-huo-sheng [2 ]
Yang, Jian [1 ]
机构
[1] Kunming Univ Sci & Technol, Fac Life Sci & Technol, Kunming 650224, Yunnan, Peoples R China
[2] Zhejiang MENOVO Pharmaceut Co Ltd, ShangYu 312300, Zhejiang, Peoples R China
来源
ZEITSCHRIFT FUR NATURFORSCHUNG SECTION B-A JOURNAL OF CHEMICAL SCIENCES | 2015年 / 70卷 / 04期
关键词
benzoquinone derivative; blanc reaction; coenzyme Q analogs; COENZYME-Q ANALOGS; UBIQUINONE; IDEBENONE; CHAIN;
D O I
10.1515/znb-2014-0208
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
The title compound (5) was prepared by a reaction sequence starting from 2,3,4,5-tetramethoxytoluene (1) via the Blanc reaction, oxidation and alkylation. The described method provides a good yield of the C-6 heterocyclic-substituted benzoquinone derivative and is suitable for the synthesis of other benzoquinone derivatives.
引用
收藏
页码:221 / 223
页数:3
相关论文
共 23 条
[1]   The antioxidant role of coenzyme Q [J].
Bentinger, Magnus ;
Brismar, Kerstin ;
Dallner, Gustav .
MITOCHONDRION, 2007, 7 :S41-S50
[2]   Coenzyme Q - Biosynthesis and functions [J].
Bentinger, Magnus ;
Tekle, Michael ;
Dallner, Gustav .
BIOCHEMICAL AND BIOPHYSICAL RESEARCH COMMUNICATIONS, 2010, 396 (01) :74-79
[3]   Complementation of coenzyme Q-deficient yeast by coenzyme Q analogues requires the isoprenoid side chain [J].
James, Andrew M. ;
Cocheme, Helena M. ;
Murai, Masatoshi ;
Miyoshi, Hideto ;
Murphy, Michael P. .
FEBS JOURNAL, 2010, 277 (09) :2067-2082
[4]   2,3-dimethoxy-5-methyl-1,4-benzoquinones and 2-methyl-1,4-naphthoquinones: glycation inhibitors with lipid peroxidation activity [J].
Jung, YS ;
Joe, BY ;
Cho, SJ ;
Konishi, Y .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2005, 15 (04) :1125-1129
[5]   Mobility and function of Coenzyme Q (ubiquinone) in the mitochondrial respiratory chain [J].
Lenaz, Giorgio ;
Genova, Maria Luisa .
BIOCHIMICA ET BIOPHYSICA ACTA-BIOENERGETICS, 2009, 1787 (06) :563-573
[6]   An improved synthesis of the "miracle nutrient" coenzyme Q10 [J].
Lipshutz, BH ;
Lower, A ;
Berl, V ;
Schein, K ;
Wetterich, F .
ORGANIC LETTERS, 2005, 7 (19) :4095-4097
[7]   Reversible Redox of NADH and NAD+ at a Hybrid Lipid Bilayer Membrane Using Ubiquinone [J].
Ma, Wei ;
Li, Da-Wei ;
Sutherland, Todd C. ;
Li, Yang ;
Long, Yi-Tao ;
Chen, Hong-Yuan .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (32) :12366-12369
[8]  
Matsumoto H., 1996, [No title captured], Patent No. [WO1996005202 A1, 1996005202]
[9]  
OKAMOTO K, 1985, CHEM PHARM BULL, V33, P3745
[10]   Photolabile ubiquinone analogues for identification and characterization of quinone binding sites in proteins [J].
Pei, Zhichao ;
Gustavsson, Tobias ;
Roth, Robert ;
Frejd, Torbjorn ;
Hagerhall, Cecilia .
BIOORGANIC & MEDICINAL CHEMISTRY, 2010, 18 (10) :3457-3466