154714-19-9

Usage

Uses

Used in Pharmaceutical Industry:
5-HYDROXY-2,2-DIMETHYL-4H-BENZO[D][1,3]DIOXIN-4-ONE is used as an intermediate in the synthesis of H946280 for its role in the development of pharmaceutical compounds. Its unique structure contributes to the formation of complex molecules with potential therapeutic applications.
Used in Biochemical Research:
In the field of biochemical research, 5-HYDROXY-2,2-DIMETHYL-4H-BENZO[D][1,3]DIOXIN-4-ONE is used as an activator of 5-lipoxygenase (5-LOX), an enzyme involved in the production of inflammatory mediators. This activation property makes it a valuable tool for studying the mechanisms of inflammation and the development of anti-inflammatory drugs.
Used in Chemical Synthesis:
5-HYDROXY-2,2-DIMETHYL-4H-BENZO[D][1,3]DIOXIN-4-ONE is also used as a key component in the synthesis of various chemical compounds, particularly those with potential applications in the pharmaceutical, agrochemical, and materials science industries. Its versatile structure allows for further functionalization and modification to create a wide range of derivatives with diverse properties and uses.

Upstream product

• 303-07-1 2,6-Dihydroxybenzoic acid 
• 67-64-1 acetone 
• 108-46-3 recorcinol 
• 699-83-2 2,6-dihydroxylacetophenone 
• 164014-40-8 2,2-dimethyl-5-trifluoromethylsulfonyloxy-4H-(1,3)benzodioxin-4-one 
• 754-05-2 ethenyltrimethylsilane 
• 888958-29-0 5-(tert-butyl-dimethyl-silanyloxy)-2,2-dimethyl-benzo[1,3]dioxin-4-one 
• 1646145-64-3 (E)-4-(2,2-dimethyl-4-oxo-4H-1,3-dioxin-6-yl)but-3-enoic acid 

Downstream Products

• 164014-40-8 2,2-dimethyl-5-trifluoromethylsulfonyloxy-4H-(1,3)benzodioxin-4-one 
• 760210-73-9 5-(benzyloxy)-2,2-dimethyl-4H-benzo[d][1,3]dioxin-4-one 
• 862298-42-8 2,2-dimethyl-5-[4-(methylsulfonyl)-2-nitrophenoxy]-4H-1,3-benzodioxin-4-one 
• 862298-40-6 4-[(2,2-dimethyl-4-oxo-4H-1,3-benzodioxin-5-yl)oxy]-N, N-dimethyl-3-nitrobenzenesulfonamide 
• 862298-43-9 2,2-dimethyl-5-[4-(morpholin-4-ylsulfonyl)-2-nitrophenoxy]-4H-1,3-benzodioxin-4-one 
• 862298-38-2 4-[(2,2-dimethyl-4-oxo-4H-1,3-benzodioxin-5-yl)oxy]-3-nitrobenzoic acid benzyl ester 
• 862298-39-3 N-{4-[(2, 2-dimethyl-4-oxo-4H-1,3-benzodioxin-5-yl)oxy]-3-nitrophenyl}-N-methylacetamide 
• 862298-77-9 4-[(2,2-dimethyl-4-oxo-4H-1,3-benzodioxin-5-yl)-oxy]-3-nitro-benzonitrile 
• 862298-36-0 2,2-dimethyl-5-[4-(5-methyl-1, 2, 4-oxadiazol-3-yl)-2-nitrophenoxy]-4H-1, 3-benzodioxin-4-one 
• 862298-37-1 5-[4-(5-cyclopropyl-1,2,4-oxadiazol-3-yl)-2-nitrophenoxy]-2, 2-dimethyl-4H-1,3-benzodioxin-4-one 
• 862298-44-0 4-[(2,2-dimethyl-4-oxo-4H-1,3-benzodioxin-5-yl) oxy]-N-ethyl-3-nitrobenzenesulfonamide 
• 675139-42-1 4-[(2,2-dimethyl-4-oxo-4H-1,3-benzodioxin-5-yl)-oxy]-3-nitro-benzoic acid methyl ester 
• 907607-49-2 methyl 2-hydroxy-6-(2-methylpropoxy)benzoate 
• 907607-23-2 methyl 2-hydroxy-6-(2,2,2-trifluoroethoxy)benzoate 

Relevant academic research and scientific papers

Divinylcarbinol Desymmetrization Strategy: A Concise and Reliable Approach to Chiral Hydroxylated Fatty Acid Derivatives

By the aid of the catalytic desymmetrization of divinylcarbinol as one-pot asymmetric induction and protection of olefin, asymmetric total syntheses of two chiral hydroxylated fatty acid derivatives were successfully achieved. The desired stereoisomers could be concisely prepared in mild conditions in a highly convergent manner. Thus, this novel strategy can help stereochemical elucidations of natural products, which have difficulties in spectroscopic stereochemical analyses due to their local symmetries in the vicinities of the stereogenic secondary hydroxyl units.

Integrating Epigenetic Modulators into NanoScript for Enhanced Chondrogenesis of Stem Cells

N-(4-Chloro-3-(trifluoromethyl)phenyl)-2-ethoxybenzamide (CTB) is a small molecule that functions by altering the chromatin architecture to modulate gene expression. We report a new CTB derivative with increased solubility and demonstrate CTB's functionality by conjugating it on the recently established NanoScript platform to enhance gene expression and induce stem cell differentiation. NanoScript is a nanoparticle-based artificial transcription factor that emulates the structure and function of transcription factor proteins (TFs) to effectively regulate endogenous gene expression. Modifying NanoScript with CTB will more closely replicate the TF structure and enhance CTB functionality and gene expression. To this end, we first conjugated CTB onto NanoScript and initiated a time-dependent increase in histone acetyltransferase activity. Next, because CTB is known to trigger the pathway involved in regulating Sox9, a master regulator of chondrogenic differentiation, we modifed a Sox9-specific NanoScript with CTB to enhance chondrogenic gene activity and differentiation. Because NanoScript is a tunable and robust platform, it has potential for various gene-regulating applications, such as stem cell differentiation.

Practical, large-scale synthesis of 2,2-dimethyl-5-hydroxy-4-oxo-benzo- 1,4-dioxin

Modification of a known procedure employing the interaction of thionyl chloride, acetone, and 2,6-dihydroxybenzoic acid was found, to provide the title compound in multikilogram quantities of acceptable yield and purity.

Enantioselective Chemical Syntheses of the Furanosteroids (-)-Viridin and (-)-Viridiol

Herein we describe concise enantioselective chemical syntheses of (-)-viridin and (-)-viridiol. Our convergent approach couples two achiral fragments of similar complexity and employs an enantioselective intramolecular Heck reaction to set the absolute stereochemical configuration of an all-carbon quaternary stereocenter. To complete the syntheses of these base- and nucleophile-sensitive natural products, we conduct carefully orchestrated site- and diastereoselective oxidations and other transformations. Our work is the first to generate these targets as single enantiomers.

Synthesis and Structure-Activity Relationship of Xenocoumacin 1 and Analogues as Inhibitors of Ribosomal Protein Synthesis

Ribosomal protein synthesis is an important target in antibacterial drug discovery. Numerous natural products have served as starting points for the development of antibiotics. We report here the total synthesis of xenocoumacin 1, a natural product that binds to 16S ribosomal RNA at a highly conserved region, as well as analogues thereof. Preliminary structure–activity relationship studies were aimed at understanding and modulating the selectivity between eukaryotic and prokaryotic ribosomes. Modifications were mainly tolerated in the aromatic region. Whole-cell activity against Gram-negative bacteria is limited by efflux and penetration, as demonstrated in genetically modified strains of E. coli. Analogues with high selectivity for eukaryotic ribosomes were identified, but it was not possible to obtain inhibitors selective for bacterial protein synthesis. Achieving high selectivity (albeit not the desired one) was thus possible despite the high homology between eukaryotic and prokaryotic ribosomes in the binding region.

Synthesis and Evaluation of Ginkgolic Acid Derivatives as SUMOylation Inhibitors

SUMOylation has emerged as an important post-translational modification that has been shown to modulate protein activity associated with various signaling pathways, and consequently, it has emerged as an important therapeutic target. While several natural products have been shown to inhibit enzymes involved in the SUMOylation process, there has been little progress toward the development of more selective and potent SUMOylation inhibitors. Ginkgolic acid was one of the first natural products discovered to inhibit the SUMO E1 enzyme. Despite its use to mechanistically investigate the SUMOylation process, ginkgolic acid also modulates other pathways as well. In this Letter, preliminary structure-activity relationships for ginkgolic acid as a SUMOylation inhibitor are presented.

PROCESS AND INTERMEDIATES FOR THE PREPARATION OF VOXELOTOR

The invention relates to a process for the preparation of Voxelotor, or a salt or solvate thereof, which comprises the use of a compound of formula (I) or (I'), or a salt or solvate thereof.

Antibacterial Anacardic Acid Derivatives

We report on the antibacterial activity of five phenolic lipids derived from anacardic acid characterized by increasing alkyl chain lengths with 6, 8, 10, 12, or 14 carbon atoms. The compounds were profiled for their physicochemical properties, transport across epithelial monolayers, cytotoxicity, and antibacterial activity as compared to common antibiotics. No cytotoxicity was reported in cell lines of fibroblast, hepatic, colorectal, or renal origin. C10 and C12 significantly increased the survival in a Galleria mellonella model infected with multi-drug-resistant Staphylococcus aureus (MRSA) or vancomycin-resistant Enterococci (VRE) as compared to the untreated control group. Future studies are required to corroborate these findings in relevant animal model systems of infection.

A Heck-Based Strategy to Generate Anacardic Acids and Related Phenolic Lipids for Isoform-Specific Bioactivity Profiling

A synthetic strategy for phenolic lipids such as anacardic acid and ginkgolic acid derivatives using an efficient and selective redox-relay Heck reaction followed by a stereoselective olefination is reported. This approach controls both the alkene position and stereochemistry, allowing the synthesis of natural and unnatural unsaturated lipids as single isomers. By this strategy, the activities of different anacardic acid and ginkgolic acid derivatives have been examined in a matrix metalloproteinase inhibition assay.

BORONIC ACID DERIVATIVES AND THERAPEUTIC USES THEREOF

Disclosed herein are antimicrobial compounds compositions, pharmaceutical compositions, the method of use and preparation thereof. Some embodiments relate to boronic acid derivatives and their use as therapeutic agents, for example, β-lactamase inhibitors (BLIs).