- Practical synthesis of 2,3-dimethoxy-6-methyl-1,4-benzoquinone-5-carboxylic acid
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2,3-Dimethoxy-6-methyl-1,4-benzoquinone-5-carboxylic acid was prepared in high yield by a reaction sequence starting from 2,3,4,5-tetramethoxytoluene (1) via a Blanc reaction, potassium dichromate oxidation, 30% H2O 2 oxidation and ceric ammonium nitrate oxidation.
- Fan, Lei,Chen, Hai-Yan,Gao, Xiao-Qiang,Gao, Xiao-Juan
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- Efficient synthesis and antioxidant activities of N-heterocyclyl substituted Coenzyme Q analogues
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A new strategy for the efficient synthesis of C-5 heterocyclyl substituted Coenzyme Q analogues was developed by N-alkylation of bromomethylated quinone 11 with a series of amines 12 under metal-free conditions. In vitro antioxidant activities of these Coenzyme Q analogues were evaluated and compared with commercial antioxidant Coenzyme Q10 by employing DPPH assay. All these N-heterocyclyl substituted Coenzyme Q analogues are found to be exhibiting good antioxidant properties and may be used as potent antioxidants for combating oxidative stress.
- Wang, Jin,Xia, Fei,Jin, Wen-Bin,Guan, Jin-Yan,Zhao, Hang
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p. 214 - 218
(2016/08/25)
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- Efficient synthesis of 2,3-dimethoxy-5-methyl-6-morpholinomethyl-1,4-benzoquinone hydrochloride
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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 derivati
- Wang, Jin,Liao, Teng-Huo-Sheng,Yang, Jian
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p. 221 - 223
(2015/06/16)
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- Efficient synthesis of 2,3,4,5-tetramethoxy-6-methylbenzoic acid
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Abstract The title compound (5), a key intermediate for preparing Coenzyme Q analogues, was prepared in a good yield by a reaction sequence starting from the 2, 3, 4, 5-Tetramethoxytoluene (1) via Blanc Reaction, Kornblum oxidation, and 30 % H2
- Wang, Jin,Zhou, Rong-Guang,Liao, Teng-Huo-Sheng,Yang, Jian
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p. 6393 - 6396
(2015/08/18)
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- Reversible redox of NADH and NAD+ at a hybrid lipid bilayer membrane using ubiquinone
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Here, we report the reversible interconversion between NADH and NAD + at a low overpotential, which is in part mediated by ubiquinone embedded in a biomimetic membrane to mimic the initial stages of respiration. This system can be used as a platform to examine biologically relevant electroactive molecules embedded in a natural membrane environment and provide new insights into the mechanism of biological redox cycling.
- Ma, Wei,Li, Da-Wei,Sutherland, Todd C.,Li, Yang,Long, Yi-Tao,Chen, Hong-Yuan
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supporting information; experimental part
p. 12366 - 12369
(2011/10/02)
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- Dual Inhibitors of Thromboxane A2 Synthase and 5-Lipoxygenase with Scavenging Activity of Active Oxygen Species. Synthesis of a Novel Series of (3-Pyridylmethyl)benzoquinone Derivatives
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A novel series of (3-pyridylmethyl)benzoquinone derivatives was molecular designed and synthesized for the dual purpose of inhibiting thromboxane A2 and leukotriene biosynthesis enzymes and scavenging active oxygen species (AOS).They were evaluated for inhibition of TXA2 synthase, inhibition of 5-lipoxygenase, and for their scavenging activity of AOS using the thiobarbituric acid method. 2,3,5-Trimethyl-6-(3-pyridylmethyl)-1,4-benzoquinone (24, CV-6504) was the most promising derivative since it showed efficient AOS scavenging activity (inhibition of lipid peroxidation in rat brain homogenates: IC50 = 1.8 10-6 M) as well as potent, specific, and well-balanced inhibitory effects on both enzymes (inhibitory effect on TXA2 synthase in human blood, IC50 = 3.3 10-7 M; inhibitory effect on 5-lipoxygenase in human blood, IC50 = 3.6 10-7 M).In adriamycin-induced proteinuria in a rat model, compound 24 at 10 mg/kg per day (po) suppressed proteinuria by more than 50percent.The proteinuria, however, could not be reduced by single administration of an inhibitor specific for thromboxane A2 synthase or for 5-lipoxygenase .The proteinuria was also not reduced by administration of an AOS scavenger, 2-O-octadecylascorbic acid (4, CV-3611).Triple function compounds such as compound 24 that specifically inhibit both enzymes as well as scavenge AOS possess a variety of pharmacologically beneficial effects.
- Ohkawa, Shigenori,Terao, Shinji,Terashita, Zen-ichi,Shibouta, Yumiko,Nishikawa, Kohei
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p. 267 - 276
(2007/10/02)
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