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Usage

Uses

Used in Skincare and Cosmetic Products:
OXO(3,4,5-TRIMETHOXYPHENYL)ACETIC ACID is used as an ingredient in skincare and cosmetic products for its antioxidant and anti-aging properties. It helps to protect the skin from environmental stressors and promotes a youthful appearance.
Used in Health Supplements:
OXO(3,4,5-TRIMETHOXYPHENYL)ACETIC ACID is used as a health supplement for its potential health benefits, including its ability to protect against oxidative stress and inflammation. It has been studied for its potential anti-cancer properties, as well as its ability to protect against cardiovascular disease and diabetes.
Used in Pharmaceutical Industry:
OXO(3,4,5-TRIMETHOXYPHENYL)ACETIC ACID is used in the pharmaceutical industry for its potential therapeutic applications. Its antioxidant properties make it a promising candidate for the development of drugs targeting various diseases, including cancer, cardiovascular disease, and diabetes.

Upstream product

• 5955-75-9 3,4,5-trimethoxybenzoyl cyanide 
• 88775-41-1 4-(3,4-methylenedioxyphenyl)-4-oxo-2-(3,4,5-trimethoxyphenyl)butyramide 
• 77-78-1 dimethyl sulfate 
• 14326-13-7 1-(1-hydroxy-2-nitroethyl)-3,4,5-trimethoxybenzene 
• 1136-86-3 methyl (3,4,5-trimethoxyphenyl) ketone 
• 4521-61-3 3,4,5-Trimethoxybenzoyl chloride 
• 109475-81-2 1-(3,4,5-trimethoxy-phenacyl)-pyridinium; chloride 
• 105905-64-4 2-chloro-1-(3,4,5-trimethoxy-phenyl)-ethanone 
• 102460-79-7 2-(4-dimethylamino-phenylimino)-3-oxo-3-(3,4,5-trimethoxy-phenyl)-propionitrile 
• 861569-57-5 (3,4,5-trimethoxy-phenyl)-glyoxylic acid amide 

Downstream Products

• 86-81-7 3,4,5-trimethoxy-benzaldehyde 
• 102026-19-7 3-(3,4,5-trimethoxy-phenyl)-1H-quinoxalin-2-one 
• 118-41-2 Eudesmic acid 
• 251909-12-3 α,α-difluoro-3,4,5-trimethoxyphenylacetic acid 
• 251909-20-3 N,N-diethyl-2,2-difluoro-2-(3,4,5-trimethoxy-phenyl)-acetamide 
• 1447331-34-1 N-(2-thiophen-2-yl-2-oxoethyl)-2-(3,4,5-trimethoxyphenyl)-2-oxoacetamide 
• 1447330-84-8 5-thiophen-2-yl-3-(3,4,5-trimethoxyphenyl)pyrazine-2(1H)-one 
• 1447331-36-3 N-[2-(3-methoxyphenyl)-2-oxoethyl]-2-(3,4,5-trimethoxyphenyl)-2-oxoacetamide 
• 1447330-86-0 5-(3-methoxyphenyl)-3-(3,4,5-trimethoxyphenyl)pyrazine-2(1H)-one 

Relevant academic research and scientific papers

Targeted Covalent Inhibition of Plasmodium FK506 Binding Protein 35

FK506-binding protein 35, FKBP35, has been implicated as an essential malarial enzyme. Rapamycin and FK506 exhibit antiplasmodium activity in cultured parasites. However, due to the highly conserved nature of the binding pockets of FKBPs and the immunosuppressive properties of these drugs, there is a need for compounds that selectively inhibit FKBP35 and lack the undesired side effects. In contrast to human FKBPs, FKBP35 contains a cysteine, C106, adjacent to the rapamycin binding pocket, providing an opportunity to develop targeted covalent inhibitors of Plasmodium FKBP35. Here, we synthesize inhibitors of FKBP35, show that they directly bind FKBP35 in a model cellular setting, selectively covalently modify C106, and exhibit antiplasmodium activity in blood-stage cultured parasites.

Metal-free benzoylation of imidazoheterocycles by oxidative decarboxylation of arylglyoxylic acids

A simple and straightforward approach has been realized for the direct benzoylation of imidazoheterocycles by oxidative decarboxylation of arylglyoxylic acids in the presence of K2S2O8 as an oxidant. Various functional groups were tolerated on both imidazoheterocycles and arylglyoxylic acids and a wide range of C5-benzoyl-imidazoheterocycles were obtained in good to high yields (50-84%). Radical trapping experiments confirmed the involvement of the radical pathway. The developed protocol is amenable for a scale-up reaction. This journal is

Method for preparing aromatic glyoxylic acid by oxidizing aromatic ethyl ketone with selenium dioxide

The invention discloses a method for preparing aromatic glyoxylic acid by oxidizing aromatic ethyl ketone with selenium dioxide. The method comprises the following steps: dissolving aromatic ethyl ketone in an alkaline organic solvent, carrying out stirri

Intermolecular Radical Addition to Ketoacids Enabled by Boron Activation

The intermolecular radical addition to the carbonyl group is difficult due to the facile fragmentation of the resulting alkoxyl radical. To date, the intermolecular radical addition to ketones, a valuable approach to construct quaternary carbon centers, remains a formidable synthetic challenge. Here, we report the first visible-light-induced intermolecular alkyl boronic acid addition to α-ketoacids enabled by the Lewis acid activation. The in situ boron complex formation is confirmed by various spectroscopic measurements and mechanistic probing experiments, which facilitates various alkyl boronic acid addition to the carbonyl group and prevents the cleavage of the newly formed C-C bond. Diversely substituted lactates can be synthesized from readily available alkyl boronic acids and ketoacids at room temperature merely under visible light irradiation, without any additional reagent. This boron activation approach can be extended to alkyl dihydropyridines as radical precursors with external boron reagents for primary, secondary, and tertiary alkyl radical additions. The pharmaceutically useful anticholinergic precursors are easily scaled up in multigrams under metal-free conditions in flow reactors.

Bioinspired Radical Stetter Reaction: Radical Umpolung Enabled by Ion-Pair Photocatalysis

A bioinspired, intermolecular radical Stetter reaction of α-keto acids and aldehydes is disclosed that is contingent on a formal “radical umpolung” concept. Enabled by secondary amine activation, electrostatic recognition ensures that the α-ketocarboxylic acids, which function as latent acyl radicals, are proximal to the in situ generated iminium salts. This photoactive contact ion pair is an electron donor–acceptor (EDA) complex, and undergoes facile single electron transfer (SET) and rapid decarboxylation prior to radical–radical recombination. Importantly, decarbonylation is mitigated by this strategy. The initial computational validation on which the process is predicated matches closely with experiment. Synergising organo- and photocatalysis activation principles finally expands the mechanistic and synthetic scope of the classic Stetter reaction to include α,β-unsaturated aldehydes as acceptors.

Optimization of potent dfg-in inhibitors of platelet derived growth factor receptorβ (PDGF-Rβ) guided by water thermodynamics

In this study we report on the hit optimization of substituted 3,5-diaryl-pyrazin-2(1H)-ones toward potent and effective platelet-derived growth factor receptor (PDGF-R) β-inhibitors. Originally, the 3,5-diaryl-pyrazin-2-one core was derived from the marine sponge alkaloid family of hamacanthins. In our first series compound 2 was discovered as a promising hit showing strong activity against PDGF-Rβ in the kinase assay (IC50 = 0.5 μM). Furthermore, 2 was shown to be selective for PDGF-Rβ in a panel of 24 therapeutically relevant protein kinases. Molecular modeling studies on a PDGF-Rβ homology model using prediction of water thermodynamics suggested an optimization strategy for the 3,5-diaryl-pyrazin-2-ones as DFG-in binders by using a phenolic OH function to replace a structural water molecule in the ATP binding site. Indeed, we identified compound 38 as a highly potent inhibitor with an IC50 value of 0.02 μM in a PDGF-Rβ enzymatic assay also showing activity against PDGF-R dependent cancer cells.

Bicyclic aza-amides for treatment of psychiatric disorders

The present invention relates to compounds of formula (I) having a bicyclic aza-amides scaffold, pharmaceutically acceptable salts of these compounds and pharmaceutical compositions containing at least one of these compounds together with pharmaceutically acceptable carrier, excipient and/or diluents. Said bicyclic aza-amides compounds can be used for prophylaxis and/or treatment of psychiatric disorders and neurodegenerative diseases, disorders and conditions.

BICYCLIC AZA-AMIDES FOR TREATMENT OF PSYCHIATRIC DISORDERS

The present invention relates to compounds of formula (I) having a bicyclic aza-amides scaffold, pharmaceutically acceptable salts of these compounds and pharmaceutical compositions containing at least one of these compounds together with pharmaceutically acceptable carrier, excipient and/or diluents. Said bicyclic aza- amides compounds can be used for prophylaxis and/or treatment of psychiatric disorders and neurodegenerative diseases, disorders and conditions.

Increasing the efficiency of ligands for FK506-binding protein 51 by conformational control

The design of efficient ligands remains a key challenge in drug discovery. In the quest for lead-like ligands for the FK506-binding protein 51 (FKBP51), we designed two new classes of bicyclic sulfonamides to probe the contribution of conformational energy in these ligands. The [4.3.1] scaffold had consistently higher affinity compared to the [3.3.1] or monocyclic scaffolds, which could be attributed to better preorganization of two key recognition motifs. Surprisingly, the binding of the rigid [4.3.1] scaffold was enthalpy-driven and entropically disfavored compared to the flexible analogues. Cocrystal structures at atomic resolution revealed that the sulfonamide nitrogen in the bicyclic scaffolds can accept an unusual hydrogen bond from Tyr113 that mimics the putative FKBP transition state. This resulted in the first lead-like, functionally active ligand for FKBP51. Our work exemplifies how atom-efficient ligands can be achieved by careful conformational control even in very open and thus difficult binding sites such as FKBP51.

Effective synthesis of 3,5-diaryl-(1H)-pyrazin-2-ones via microwave mediated ring closure

In this study we report on a flexible straight forward synthesis toward novel 3,5-diaryl-(1H)-pyrazin-2-ones. Our synthetic strategy involved an acyclic di-keto derivative as key intermediate. The final pyrazin-2-one ring closure reaction was yield-optimized by using a microwave mediated procedure and ammoniumacetate as nitrogen source. Our method is a suitable alternative to palladium-catalyzed coupling reactions for the 3,5-diaryl decoration of the (1H)-pyrazin-2-one scaffold. Since the (1H)-pyrazin-2-ones is present as scaffold in a number of biologically active compounds the reported synthetic platform is a useful approach to generate a set of highly diverse 3,5-diaryl-(1H)-pyrazin-2-one compounds.