71582-59-7

Upstream product

• 93006-13-4 1-<2,5-bis(acetyloxy)-3,4-dimethylphenyl>ethanone 
• 608-43-5 2,3-dimethyl-1,4-dihydroxybenzene 
• 334868-40-5 1-(2-hydroxy-5-acetoxy-3,4-dimethyl-phenyl)-ethanone 
• 98-86-2 acetophenone 
• 64-19-7 acetic acid 

Downstream Products

• 93006-13-4 1-<2,5-bis(acetyloxy)-3,4-dimethylphenyl>ethanone 
• 78752-01-9 2-acetyl-5,6-dimethyl-1,4-benzoquinone 
• 153752-58-0 1-<5-(acetyloxy)-2-hydroxy-3,4-dimethylphenyl>-1,3-butanedione 
• 581807-59-2 1-[2-hydroxy-3,4-dimethyl-5-(tetrahydro-pyran-2-yloxy)-phenyl]-ethanone 
• 1352754-55-2 1-(5-((dimethyl-tert-butylsilyl)oxy)-2-methoxy-3,4-dimethylphenyl)ethanone 
• 1352754-56-3 5-(dimethyl-tert-butylsilyl)oxy-2-methoxy-3,4-dimethylphenyl acetate 
• 1352754-57-4 5-(dimethyl-tert-butylsilyl)oxy-2-methoxy-3,4-dimethylphenol 
• 1352754-58-5 2-(2-(dimethyl-tert-butylsilyl)oxy-6-hydroxy-5-methoxy-3,4-dimethylphenylthio)isoindoline-1,3-dione 
• 1352754-59-6 5-(dimethyl-tert-butylsilyl)oxy-2,3-dihydro-8-methoxy-2-(4-methoxyphenyl)-6,7-dimethylbenzo[b][1,4]oxathiine 
• 1352754-60-9 2,3-dihydro-8-methoxy-2-(4-methoxyphenyl)-6,7-dimethylbenzo[b][1,4]oxathiin-5-ol 
• 1352754-71-2 2,3-dihydro-2-(4-methoxyphenyl)-6,7-dimethylbenzo[b][1,4]oxathiine-5,8-dione 
• 1352754-54-1 1-(5-((dimethyl-tert-butylsilyl)oxy)-2-hydroxy-3,4-dimethylphenyl)ethanone 

Relevant academic research and scientific papers

Synthesis and pharmacological evaluation of acylhydroquinone derivatives as potent antiplatelet agents

Platelets are the smallest blood cells, and their activation (platelet cohesion or aggregation) at sites of vascular injury is essential for thrombus formation. Since the use of antiplatelet therapy is an unsolved problem, there are now focused and innovative efforts to develop novel antiplatelet compounds. In this context, we assessed the antiplatelet effect of an acylhydroquinone series, synthesized by Fries rearrangement under microwave irradiation, evaluating the effect of diverse acyl chain lengths, their chlorinated derivatives, and their dimethylated derivatives both in the aromatic ring and also the effect of the introduction of a bromine atom at the terminus of the acyl chain. Findings from a primary screening of cytotoxic activity on platelets by lactate dehydrogenase assay identified 19 non-toxic compounds from the 27 acylhydroquinones evaluated. A large number of them showed IC50 values less than 10 μM acting against specific pathways of platelet aggregation. The highest activity was obtained with compound 38, it exhibited sub-micromolar IC50 of 0.98 ± 0.40, 1.10 ± 0.26, 3.98 ± 0.46, 6.79 ± 3.02 and 42.01 ± 3.48 μM against convulxin-, collagen-, TRAP-6-, PMA- and arachidonic acid-induced platelet aggregation, respectively. It also inhibited P-selectin and granulophysin expression. We demonstrated that the antiplatelet mechanism of compound 38 was through a decrease in a central target in human platelet activation as in mitochondrial function, and this could modulate a lower response of platelets to activating agonists. The results of this study show that the chemical space around ortho-carbonyl hydroquinone moiety is a rich source of biologically active compounds, signaling that the acylhydroquinone scaffold has a promising role in antiplatelet drug research.

Synthesis of antiplatelet ortho-carbonyl hydroquinones with differential action on platelet aggregation stimulated by collagen or TRAP-6

Cardiovascular diseases are the leading cause of death in the world. Platelets have a major role in cardiovascular events as they bind to the damaged endothelium activating and forming thrombi. Although some hydroquinone scaffold-containing compounds have known antiplatelet activities, currently there is a lack of evidence on the antiplatelet activity of hydroquinones carrying electron attractor groups. In this work, we evaluate the antiplatelet effect of a series of ortho-carbonyl hydroquinone derivatives on cytotoxicity and function of human platelets, using collagen and thrombin receptor activator peptide 6 (TRAP-6) as agonists. Our structure-activity relationship study shows that gem-diethyl/methyl substitutions and the addition/modifications of the third ring of ortho-carbonyl hydroquinone scaffold influence on the selective index (IC50 TRAP-6/IC50 Collagen) and the inhibitory capacity of platelet aggregation. Compounds 3 and 8 inhibit agonist-induced platelet aggregation in a non-competitive manner with IC50 values of 1.77 ± 2.09 μM (collagen) and 11.88 ± 4.59 μM (TRAP-6), respectively and show no cytotoxicity. Both compounds do not affect intracellular calcium levels and mitochondrial bioenergetics. Consistently, they reduce the expression of P-selectin, activation of glycoprotein IIb/IIIa, and release of adenosine triphosphate and CD63 from platelet. Our findings may be used for further development of new drugs in platelet-related thrombosis diseases.

Assessing parameter suitability for the strength evaluation of intramolecular resonance assisted hydrogen bonding in O-carbonyl hydroquinones

Intramolecular hydrogen bond (IMHB) interactions have attracted considerable attention due to their central role in molecular structure, chemical reactivity, and interactions of biologically active molecules. Precise correlations of the strength of IMHB’s with experimental parameters are a key goal in order to model compounds for drug discovery. In this work, we carry out an experimental (NMR) and theoretical (DFT) study of the IMHB in a series of structurally similar o-carbonyl hydroquinones. Geometrical parameters, as well as Natural Bond Orbital (NBO) and Quantum Theory of Atoms in Molecules (QTAIM) parameters for IMHB were compared with experimental NMR data. Three DFT functionals were employed to calculated theoretical parameters: B3LYP, M06-2X, and ωB97XD. O . . . H distance is the most suitable geometrical parameter to distinguish among similar IMHBs. Second order stabilization energies ?Eij(2) from NBO analysis and hydrogen bond energy (EHB) obtained from QTAIM analysis also properly distinguishes the order in strength of the studied IMHB. ?Eij(2) from NBO give values for the IMHB below 30 kcal/mol, while EHB from QTAIM analysis give values above 30 kcal/mol. In all cases, the calculated parameters using ωB97XD give the best correlations with experimental1H-NMR chemical shifts for the IMHB, with R2 values around 0.89. Although the results show that these parameters correctly reflect the strength of the IMHB, when the weakest one is removed from the analysis, arguing experimental considerations, correlations improve significantly to values around 0.95 for R2

Optimization of the antioxidant activity of hydroxy-substituted 4-thiaflavanes: A proof-of-concept study

The design and the synthesis of a new family of hydroxy-4-thiaflavanes, in which the reactive phenolic OH is ortho to the sulfur atom of the benzofused oxathiin ring, allowed to prepare antioxidants that show rate constants for the reaction with peroxyl radicals (kinh), and bond dissociation energies (BDE), of the ArO-H group identical to those of α-tocopherol, the main component of vitamin E and the most effective lipophilic antioxidant known in nature. The peculiar conformation of the six-membered heterocyclic ring prevents the formation of an intramolecular hydrogen bond between the OH group and the S atom, while ensuring a good stabilization by electron donation of the phenoxyl radical formed after the reaction with peroxyl radicals. The preparation of these compounds was achieved through an inverse electron demand hetero Diels-Alder reaction of styrenes with o-thioquinones, in turn prepared from accurately designed 1,3-dihydroxy arenes. Properly arranging the substitution pattern on the aromatic ring, as in derivatives 9 and 11, allowed to reach values of kinh up to 4.0× 106 M-1 s -1 and BDE(OH) of 77.2 kcal mol-1. This approach represents an innovative way to obtain highly active antioxidants without using strongly electron donating alkylamino groups which are associated with adverse toxicological profiles. Sulfur makes the difference (again): The stereoelectronic features triggered by the sulfur atom in the benzo-fused six-membered ring of 4-thiaflavanes have been exploited to design a new family of phenolic antioxidants that show an ability to react with peroxyl radicals identical to that of α-tocopherol, the main component of vitamin E and the most potent natural lipophilic antioxidant (see scheme). Copyright

Spiro derivatives as lipoxygenase inhibitors

The present invention is concerned with certain novel spiro substituted heterocylic ring derivatives. These compounds may be useful in the manufacture of pharmaceutical compositions for treating disorders mediated by lipoxygenases. They may also be useful

Benzofuran derivatives

Certain benzofuran derivatives are useful in the treatment of certain ischemic or inflammatory conditions, as well as neuroinflammation, neurodegeneration or degenerative diseases in which mitochondrial dysfunction leads to tissue degeneration. They are a

Cytoprotective benzofuran derivatives

Cytoprotective compounds, many of which are benzofuran derivatives are useful in the treatment of certain ischemic or inflammatory conditions, including but not limited to stroke, myocardial infarction, congestive heart failure, and skin disorders charact