- AgNO3-catalyzed decarboxylative cross-coupling reaction: an approach to coenzyme Q
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An efficient and general method for the synthesis of coenzyme Q compounds through the activation of the 1,4-benzoquinone Csp2-H bond has been developed. This C-C bond formation reaction proceeds readily in an open flask by the direct cross-coupling reaction of coenzyme Q0with commercially available aliphatic carboxylic acids utilizing AgNO3as a catalyst and K2S2O8as an oxidant in aqueous solution. This radical reaction is operationally simple and amenable to gram-scale synthesis.
- Luo, Wan-Yue,Lu, Bin,Qiu, Yong-Fu,Zhou, Rong-Ye,He, Yong-Jing,Wang, Jin
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Read Online
- Coenzyme Q compound synthesis method
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The invention relates to a coenzyme Q compound synthesis method, which comprises the steps of: dissolving substituted or unsubstituted 3, 4, 5-trimethoxytoluene in an organic solvent, carrying out a reaction on the obtained solution and an oxidant aqueous solution for 1-2h at a temperature of 20-80 DEG C under the catalysis of an acid, and carrying out extraction, water washing, reduced pressure distillation and recrystallization on the obtained crude product to obtain a coenzyme Q compound. Raw materials used in the method are cheap and easy to obtain, and no toxic or harmful waste gas or waste residue is generated in the reaction process; and reaction steps are few, the operation is easy and convenient, the product yield is high, and the method is suitable for industrial large-scale production.
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Paragraph 0037
(2020/11/01)
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- COMPOUND CONTAINING INDOLEACETIC ACID CORE STRUCTURE AND USE THEREOF
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Disclosed are a compound as shown by the following formula 1, and a pharmaceutically acceptable salt, an ester, a hydrate and an organic solvate thereof. In the formula (1), the groups R1 to R17 are independently selected from the group consisting of hydrogen, fluorine, chlorine, bromine, iodine, C1-C8 alkyl, C1-C8 alkoxy, carbonyl, hydroxyl, amino, azido, carboxyl and C1-C8 alkylsulfinyl, respectively; and X is a carbon or nitrogen atom; Y is selected from the following groups: a single bond, C1-C8 alkylene, C6-C20 arylene and C4-C20 heteroarylene; and n is an integer from 5 to 20. Also provided in the present invention are a pharmaceutical composition containing the compound, and use thereof in the field of tumor therapy.
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- A preparation method of idebenone (by machine translation)
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The invention relates to a preparation method of idebenone, the method comprises: to coenzyme Q0 and 11 - hydroxy undecanoic acid as the raw material, the choice of copper chloride, copper sulfate, copper acetate, silver carbonate, silver oxide, palladium chloride or palladium acetate in a metal salt as a catalyst, in the protection of the next adds oxygen oxidizing agent hydrogen peroxide, alkylation of the free radical reaction. The reaction system by extraction, water washing, drying, reduced pressure distillation, column chromatography, get the yellow needle-like crystal, 6 - (10 - hydroxyl decyl) - 2, 3 - dimethoxy - 5 - methyl - 1, 4 - benzoquinone, namely idebenone. This preparation method has a simple operation, low cost, and the yield and the like, suitable for large-scale industrial production of idebenone. (by machine translation)
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Paragraph 0021; 0024; 0026; 0028; 0030; 0032; 0034
(2017/09/01)
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- Single-step synthesis of idebenone from Coenzyme Q0 via free-radical alkylation under silver catalysis
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Idebenone was synthesized directly by free-radical alkylation of 2,3-dimethyl-1,4-benzoquinone (Coenzyme Q0) with commercially available 11-hydroxyundecanoic acid in the presence of potassium peroxodisulfate and silver nitrate in a mixed solvent (CH3CN-H2O, 1:1) under mild condition in good yields (65%, based on Coenzyme Q0). The reaction is operationally simple and could be used in the preparation of other biologically Coenzyme Q analogues.
- Wang, Jin,Li, Shuo,Yang, Tao,Yang, Jian
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p. 9029 - 9032
(2015/03/05)
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- Synthetic route discovery and introductory optimization of a novel process to idebenone
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An environmentally benign, convenient, high yielding, and cost-effective synthesis leading to idebenone is disclosed. The synthesis includes a bromination process for the preparation of 2-bromo-3,4,5-trimethoxy-1- methylbenzene, a protocol for the Heck cross-coupling reaction using either thermal or microwave heating, olefin reduction by palladium catalyzed hydrogenation, and a green oxidation protocol with hydrogen peroxide as oxidant to achieve the benzoquinone framework. The total synthesis is composed of six steps that provide an overall yield of 20% that corresponds to a step yield of 76%.
- Tsoukala, Anna,Bjorsvik, Hans-Rene
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p. 673 - 680
(2011/12/01)
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- Synthesis and characterization of mitoQ and idebenone analogues as mediators of oxygen consumption in mitochondria
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Analogues of mitoQ and idebenone were synthesized to define the structural elements that support oxygen consumption in the mitochondrial respiratory chain. Eight analogues were prepared and fully characterized, then evaluated for their ability to support oxygen consumption in the mitochondrial respiratory chain. While oxygen consumption was strongly inhibited by mitoQ analogues 2-4 in a chain length-dependent manner, modification of idebenone by replacement of the quinone methoxy groups by methyl groups (analogues 6-8) reduced, but did not eliminate, oxygen consumption. Idebenone analogues 6-8 also displayed significant cytoprotective properties toward cultured mammalian cells in which glutathione had been depleted by treatment with diethyl maleate.
- Duveau, Damien Y.,Arce, Pablo M.,Schoenfeld, Robert A.,Raghav, Nidhi,Cortopassi, Gino A.,Hecht, Sidney M.
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experimental part
p. 6429 - 6441
(2010/10/03)
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- Esters of long-chain alcohols and preparation thereof
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Disclosed are esters and a process for the preparation of the esters represented by formula 1: The process includes reacting an alcohol with a long-chain acid R2COOH or long-chain ester R2COOR4 in the presence of an organic solvent and an enzyme with or without the removal of water.
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- ESTERS OF LONG-CHAIN ALCOHOLS AND PREPARATION THEREOF
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Disclosed is a composition and methods of treating a skin condition. The ester includes an ester and a dermatologically acceptable carrier. The ester is represented by the general formula 1:
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- Synthesis of idebenone; a synthetic analog of coenzyme Q
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Idebenone, a synthetic analog of coenzyme Q, was prepared from the tetramethoxytoluene 2. Two main transformations in this procedure are Friedel-Crafts acylation of 2 to 4 and CAN assisted oxidation of 7 to the quinone 8.
- Jung,Joe,Seong,Park
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p. 2735 - 2741
(2007/10/03)
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- Spherical granules having core and their production
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The spherical granules having a core coated with spraying powder containing a drug and low substituted hydroxypropylcellulose, because of their excellent hardness, can be coated further evenly, (e.g. sustained release coating, gastric coating, enteric coating), and at the time the granules are excellent in disintegration.
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- Reduction of carboxylic esters
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A method for producing a compound of the formula: STR1 [wherein R1 and R2 each stand for a lower alkyl group; n denotes an integer of 0 to 21; X stands for hydrogen atom or an optionally protected hydroxyl group; and Y stands for an optionally protected hydroxyl group], which comprises reducing an ester compound of the formula: STR2 [wherein R1, R2, n, X and Y are of the same meaning as defined above, and R3 stands for a lower alkyl group ] with a mixture of sodium borohydride and aluminum chloride. This method give the desired compound in a high yield, and is advantageous from the industrial point of view.
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- Method of producing quinone derivatives
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A quinone compound of the formula: STR1 wherein R stands for an alkyl group of 1 to 22 carbon atoms having at its terminal end a hydroxyl group which may be protected, can be obtained with industrial advantage by allowing a compound of the formula: STR2 t
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- Aralkyl carboxylic acid compounds
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Novel compounds of the formulae STR1 wherein R represents lower alkyl or lower alkoxy, A represents --CH2 --, --CO-- or STR2 n represents an integer of 1 to 8, X represents hydrogen or hydroxyl which may be protected and Y represents hydroxyl which may be protected, and their esters show an excellent action on the lysosomal membranes of cells, and exhibit excellent pharmacological activities such as physiologic host defense control activity, especially immuno-potentiating activity.
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