- Efficient synthesis of 5-bromo-2,3-dimethoxy-6-methyl-1,4-benzoquinone: key intermediate for preparing Coenzyme Q
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The title compound, a key intermediate for preparing Coenzyme Qn family, was prepared in an excellent yield by a reaction sequence starting from the commercially available 3,4,5-trimethoxytoluene 1 via bromination, methoxylation and oxidation reactions. A
- Qiu, Yong-Fu,Lu, Bin,Yan, Yi-Yu,Luo, Wan-Yue,Wang, Jin,Hu, Xiao
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p. 2745 - 2748
(2019/08/21)
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- 2,3-Dimethoxy-5-methyl-1,4-benzoquinones and 2-methyl-1,4-naphthoquinones: Glycation inhibitors with lipid peroxidation activity
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Anti-glycation activity of our anti-oxidant quinone library was measured and several 2,3-dimethoxy-5-methyl-1,4-benzoquinones and 2-methyl-1,4- naphthoquinones were identified as novel inhibitors of glycation, of which 2,3-dimethoxy-5-methyl-1,4-benzoquinones 13b is the most potent glycation inhibitor with around 50 μM of the IC50 value.
- Jung, Young-Sik,Joe, Bo-Young,Cho, Sung Ju,Konishi, Yasuo
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p. 1125 - 1129
(2007/10/03)
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- A new fluorogenic transformation: Development of an optical probe for coenzyme Q
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(Chemical Equation Presented) A new fluorogenic transformation based on a quinone reduction/lactonization sequence has been developed and evaluated as a tool for probing redox phenomena in a biochemical context. The probe presented herein is an irreversible redox probe and is reduced selectively by biologically relevant quinols such as ubiquinol but is inert to reduced nicotinamides (e.g., NADH). The ensuing cyclization is fast and quantitative and provides a measurable optical response.
- Tremblay, Matthew S.,Sames, Dalibor
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p. 2417 - 2420
(2007/10/03)
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- The preparation of side chain functionalized analogues of coenzyme Q for protein conjugation studies
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The synthesis of two analogues of CoQ (10 and 13) suitable for conjugation to a peptide or protein, and hence the development of an ELISA immunoassay, is presented. These analogues were synthesized from the protected quinone, 1-bromo-2-methyl-3,4,5,6-tetramethoxybenzene (1), itself prepared from commercially available CoQ-0 (3). Model coupling studies of one of the analogues (10) to N-acetyl-L-lysine methyl ester and a lysine containing dipeptide (N-acetylglycine-L-lysine methyl ester) were also undertaken as a first step to monoclonial antibody production.
- Daines, Alison M.,Abell, Andrew D.
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p. 2371 - 2375
(2007/10/03)
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- SYNTHESIS OF UBIQUINONE AND MENAQUINONE ANALOGUES BY OXIDATIVE DEMETHYLATION OF ALKENYLHYDROQUINONE ETHERS WITH ARGENTIC OXIDE OR CERIC AMMONIUM NITRATE IN THE PRESENCE OF 2,4,6-PYRIDINE-TRICARBOXYLIC ACID
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It was found that alkenylhydroquinone ethers demethylated with argentic oxide or ceric ammonium nitrate in the presence of 2,4,6-pyridinetricarboxylic acid as a catalyst and afforded ubiquinone-2, menaquinone-2 and their analogs in yields of 53 to 89 percent.The new approach to the synthesis of starting alkenylhydroquinone ethers as well as 2,4,6-pyridinetricarboxylic acid and its derivatives has been reported.
- Syper, L.,Kloc, K.,Mlochowski, J.
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p. 123 - 129
(2007/10/02)
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