6293-55-6

Upstream product

• 609-22-3 2,4-dibromo-6-methylphenol 
• 13070-29-6 5,6-dibromo-2-methyl-cyclohex-2-ene-1,4-dione 
• 50848-60-7 2-bromo-6-methylbenzene-1,4-diol 
• 20834-60-0 2-bromo-4-(tert-butyl)-6-methylphenol 
• 95-48-7 ortho-cresol 
• 98-27-1 2-Methyl-4-t-butylphenol 
• 553-97-9 2-Methyl-1,4-benzoquinone 
• 85911-53-1 5-bromo-6-hydroxy-toluene-3-sulfonic acid 
• 64-17-5 ethanol 

Downstream Products

• 50848-60-7 2-bromo-6-methylbenzene-1,4-diol 
• 129332-56-5 3-Bromo-2-heptyl-5-methyl-[1,4]benzoquinone 
• 129332-57-6 5-bromo-3-methyl-6-nonyl-1,4-benzoquinone 
• 99933-69-4 3-(4-Methoxy-phenyl)-6-methyl-1H-benzo[1,3,4]oxadiazine-5,8-dione 
• 99933-67-2 6-Methyl-3-phenyl-1H-benzo[1,3,4]oxadiazine-5,8-dione 
• 99933-72-9 3-(2-Hydroxy-phenyl)-6-methyl-1H-benzo[1,3,4]oxadiazine-5,8-dione 
• 99933-73-0 3-(4-Chloro-phenyl)-6-methyl-1H-benzo[1,3,4]oxadiazine-5,8-dione 
• 135082-78-9 2-anilino-3-bromo-5-methyl-1,4-benzoquinone 
• 99933-68-3 6-Methyl-3-p-tolyl-1H-benzo[1,3,4]oxadiazine-5,8-dione 
• 129332-55-4 3-Bromo-5-methyl-2-pentyl-[1,4]benzoquinone 
• 99933-75-2 3-Benzyl-6-methyl-1H-benzo[1,3,4]oxadiazine-5,8-dione 
• 125318-21-0 (E)-3-(4-chloro-3-methyl-2-butenyl)-2,5-bis(methoxymethoxy)toluene 
• 50848-61-8 1-bromo-2,5-bis(methoxymethoxy)-3-methylbenzene 
• 125318-29-8 3-allyl-2,5-bis(methoxymethoxy)toluene 

Relevant academic research and scientific papers

Synthesis and antitumor activity evaluation of compounds based on toluquinol

Encouraged by the promising antitumoral, antiangiogenic, and antilymphangiogenic properties of toluquinol, a set of analogues of this natural product of marine origin was synthesized to explore and evaluate the effects of structural modifications on their cytotoxic activity. We decided to investigate the effects of the substitution of the methyl group by other groups, the introduction of a second substituent, the relative position of the substituents, and the oxidation state. A set of analogues of 2-substituted, 2,3-disubstituted, and 2,6-disubstituted derived from hydroquinone were synthesized. The results revealed that the cytotoxic activity of this family of compounds could rely on the hydroquinone/benzoquinone part of the molecule, whereas the substituents might modulate the interaction of the molecule with their targets, changing either its activity or its selectivity. The methyl group is relevant for the cytotoxicity of toluquinol, since its replacement by other groups resulted in a significant loss of activity, and in general the introduction of a second substituent, preferentially in the para position with respect to the methyl group, was well tolerated. These findings provide guidance for the design of new toluquinol analogues with potentially better pharmacological properties.

A Platform of Regioselective Methodologies to Access Polysubstituted 2-Methyl-1,4-naphthoquinone Derivatives: Scope and Limitations

A platform of synthetic methodologies has been established to access a focused library of polysubstituted 3-benzylmenadione derivatives functionalized on the aromatic ring of the naphthoquinone core. Two main routes were explored: 1) The naphthol route, starting from either an α-tetralone or a propiophenone, and 2) the regioselective Diels-Alder reaction, starting from various dienes and two 2-bromo-5(or 6)-methyl-1,4-benzoquinones. 6-Substituted 2-methylnaphthols were synthesized by using a xanthate-mediated free-radical addition/cyclization sequence for the construction of the 6-substituted menadione subunit. Furthermore, an efficient and simple new pathway that allows the formation of 6- or 7-substituted 3-(substituted-benzyl)menadione regioisomers from a common commercial scaffold has also been developed by the naphthol route, advantageous with regard to step economy. Our synthetic methodologies exemplified by 34 compounds have allowed structure-activity relationships to be deduced for use as the basis for the development of new antimalarial redox-active polysubstituted benzylmenadione derivatives.

Synthesis and biological evaluation of 1,4-naphthoquinones and quinoline-5,8-diones as antimalarial and schistosomicidal agents

Improving the solubility of polysubstituted 1,4-naphthoquinone derivatives was achieved by introducing nitrogen in two different positions of the naphthoquinone core, at C-5 and at C-8 of menadione through a two-step, straightforward synthesis based on the regioselective hetero-Diels-Alder reaction. The antimalarial and the antischistosomal activities of these polysubstituted aza-1,4-naphthoquinone derivatives were evaluated and led to the selection of distinct compounds for antimalarial versus antischistosomal action. The AgII-assisted oxidative radical decarboxylation of the phenyl acetic acids using AgNO3 and ammonium peroxodisulfate was modified to generate the 3-picolinyl-menadione with improved pharmacokinetic parameters, high antimalarial effects and capacity to inhibit the formation of β-hematin. The Royal Society of Chemistry 2012.

Biomimetic synthesis of (-)-pycnanthuquinone C through the diels-alder reaction of a vinyl quinone

Three strikes and you're out! A concise, asymmetric synthesis of pycnanthuquinone C underscores the biosynthetic relevance of Diels-Alder reactions of vinyl quinones. The relative and absolute configuration of the natural product has been elucidated.

A stereocontrolled synthesis of δ-trans-tocotrienoloic acid

(Chemical Equation Presented) A consise stereoselective total synthesis of a naturally occurring polymerase β inhibitor, δ-trans-tocotrienoloic acid (2), is described. The key step in the synthesis is an acid-catalyzed cyclodehydration reaction. Additiona

Bromoquinone-enaminone annulations: Syntheses of murrayaquinone-A and (±)-bismurrayaquinone-A

A total synthesis of the carbazolequinone alkaloid, murrayaquinone-A was achieved by an initial annulation of the N-benzyl enamine 8 with 2-methyl-5-bromobenzoquinone 6. Shapiro deoxygenation-olefination followed by heating with DDQ resulted in the exclusive formation of N-benzylmurrayaquinone-A 16. Debenzylation proved very difficult but was finally achieved by heating briefly in trifluoroacetic acid with a catalytic quantity of trifluoromethanesulfonic acid. A single dimeric annulation side product was also formed in the annulation reaction. By using the same synthetic sequence as was employed in the synthesis of 1, the N,N-bis-p-methoxybenzyl dimer 13 was successfully converted to (±)-bismurrayaquinone-A 5.

Solid state redox chemistry of hydroquinones and quinones

Solid state ceric ammonium nitrate (CAN) oxidation of hydroquinones to the corresponding quinones, gives best results when operating with ultrasonic irradiation. Nitrogen dioxide plays a key role in these 'solid-solid' oxidations. The oxidation of hydroquinones to quinones can also be achieved in a unique 'solid-solid-solid' reaction, i.e., by using a limited amount of CAN in the presence of a full equivalent of a solid cooxidant such as KBrO3. Reduction of quinones with sodium dithionite in the solid state gives rise to the corresponding highly colored quinhydrones and, eventually, to hydroquinones.

Synthesis and inhibitory activity of bromoquinone derivatives

2,5 Dibromo-3-methyl-6-isopropyl-1,4-benzoquinone has been reported inhibitory to b6-f and b-c1 complexes [Malkin, R. (1977) Biochim. Biophys. Acta., 501, 552-554]. In this paper, four classes of the analogues are synthesized. They were 5-bromo-3-methyl, 3-bromo-2-methoxy-5-methyl, 2,5-dibromo-3-methyl, and 3,5-dibromo-2-methyl derivatives with the side chain -(CH2)nH of N=5,7,9,11 and 13 at position 6. Dibromo compounds are usually more inhibitory in the mitochondrial ubiquinol cytochrome c reductase; the maximal inhibition was usually with 9 methylene in a functional group.

SYNTHESIS AND STRUCTURE REVISION OF BIFURCARENONE, A UNIQOE MONOCYCLIC DITERPENE IN COMBINATION WITH A HYDROQUINONE C7 UNIT AS AN INHIBITOR OF MITOTIC CELL DIVISION

Bifurcarenone, a C27 hydroquinone isolated from the brown seaweed Bifurcaria galapegensis, was synthesized as its racemate, and shown to be 2.The structure 1, originally proposed for bifurcarenone, was synthesized, and found to be different from the natur

Facile Oxidation of Halophenols and Halonaphthols by Ceric Ammonium Sulphate and Manganic Sulphate

Ce(IV) and Mn(III) sulphates oxidise halophenols and halonaphthols in aqueous acetonitrile medium to the corresponding haloquinones in high yields.