30685-17-7

Upstream product

• 605-94-7 2,3-Dimethoxy-5-methyl-1,4-benzoquinone 
• 73875-27-1 2,3,4,5-tetramethoxy-6-methyl-1-bromobenzene 
• 72326-72-8 2-bromo-3,4,5-trimethoxy-1-methylbenzene 
• 6443-69-2 3,4,5-trimethoxytoluene 

Downstream Products

• 34417-79-3 2-bromo-5,6-dimethoxy-3-methylbenzene-1,4-diol 
• 727-81-1 2,3-dimethoxy-5-methyl-6-(3-methyl-2-butenyl)-1,4-benzoquinone 
• 34407-31-3 1-bromo-3,4-dimethoxy-2,5-bis(methoxymethoxy)-6-methylbenzene 

Relevant academic research and scientific papers

Efficient synthesis of 5-bromo-2,3-dimethoxy-6-methyl-1,4-benzoquinone: key intermediate for preparing Coenzyme Q

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

Electrochemical chlorination and bromination of electron-deficient C[sbnd]H bonds in quinones, coumarins, quinoxalines and 1,3-diketones

The electrochemistry-promoted chlorination and bromination of electron-deficient C[sbnd]H bonds was developed, using quinones, coumarins, quinoxalines and 1,3-diketones. This protocol features readily available and safe halogen sources (hydrochloric acid and KBr), high site-selectivity and mild reaction conditions. It could provide an efficient access to a series of chlorinated and brominated quinones, coumarins, quinoxalines and 1,3-diketones.

Coenzyme Q compound synthesis method

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.

Rational design, synthesis and biological evaluation of ubiquinone derivatives as IDO1 inhibitors

Indoleamine 2,3-dioxygenase 1 (IDO1) is an attractive therapeutic target for the treatment of cancer, chronic viral infections and neurological disorders characterized by pathological immune stimulation. Herein, a series of known metal-chelating ubiquinone derivatives were designed, synthesized and evaluated for the IDO1 inhibiting activities. The docking studies showed that the compounds 11, 16, 18 and coenzyme-Q1 exhibited different binding modes to IDO1 protein. Among these compounds, the most active compound is 16d with an IC50 of 0.13 μM in enzymatic assay. The results reveal that a possible halogen bonding interaction between the bromine atom (3-Br) and Cys129 significantly enhances the inhibition activity against IDO1. This study provides structural insights of the interactions between ubiquinone analogues and IDO1 protein for the further modification and optimization.

Photochromic coenzyme Q derivatives: Switching redox potentials with light

Coenzyme Q is an important redox cofactor involved in a variety of cellular processes, and is thus found in several cell compartments. We report a photochromic derivative of coenzyme Q that combines the molecular structures of the redox active cofactor and a photochromic dye. Light irradiation triggers an electronic rearrangement reversibly changing the redox potential. We used this effect to control the intermolecular redox reaction of the photochromic coenzyme Q derivative with dihydropyridine in solution by light irradiation. On mitochondria, the altered redox properties showed an effect on the respiratory chain. The experiments demonstrate that the redox reactions can be initiated inside the system of interest through irradiation with light and the accompanied photoisomerization.

Thiol-ubiquinone assisted fragmentation of gold nanoparticles

We report the spontaneous fragmentation of gold nanoparticles (AuNPs) induced, in aqueous solution at room temperature, by thiol derivative of ubiquinone, which involves the energetic electron injection from thiol-ubiquinone to the gold nanoparticles. The

In situ spectroeletrochemistry and cytotoxic activities of natural ubiquinone analogues

Quinones are a group of potent antineoplastic agents. Here we described effective and facile routes to synthesize a series of ubiquinone analogues (UQAs). These unique compounds have been investigated by electrochemistry and in situ UV-vis spectroelectrochemistry to explore their electron-transfer processes and radical properties in aprotic media. The structure-activities relationships of inhibiting cancer cell proliferation of UQAs were examined in murine melanoma B16F10 cells using a 72 h continuous exposure MTT (3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide) assay. Our results revealed that UQAs had improved antiproliferative activity and displayed better inhibitory effects than natural ubiquinone 10. The cytotoxic activities of UQAs were correlated to the semiubiquinone radicals, which were confirmed by in situ electron spin resonance (ESR). In the cytotoxicity test, 6-vinylubiquinone 5 and 6-(4′-fluorophenyl) ubiquinone 7 that possess half maximal inhibitory concentration value (IC50) of 6.1 μM and 6.2 μM. This would make them as valuable candidates for future pharmacological studies.