38480-94-3

Usage

Uses

Used in Pharmaceutical Industry:
2',3'-DIMETHOXYACETOPHENONE is used as a reactant for the preparation of quinazolinone hybrids, which exhibit antileishmanial activity. These hybrids are being developed as potential treatments for Leishmaniasis, a disease caused by protozoan parasites that affect various tissues in the human body.
Additionally, 2',3'-DIMETHOXYACETOPHENONE may also be used in other applications within the pharmaceutical industry, such as the synthesis of other bioactive compounds or as a building block for the development of new drugs.

Preparation

Obtained by heating its oxime with pyridinium chloride containing 5% of water (35%).

Upstream product

• 917-64-6 methyl magnesium iodide 
• 5653-62-3 2,3-dimethoxybenzonitrile 
• 6848-73-3 1-(2,3-dimethoxyphenyl)-1-ethanol 
• 141-97-9 ethyl acetoacetate 
• 7169-06-4 2,3-dimethoxybenzoyl chloride 
• 105-53-3 diethyl malonate 
• 506-82-1 dimethylcadmium 
• 7664-93-9 sulfuric acid 
• 528830-98-0 ethyl 3-(2,3-dimethoxyphenyl)-3-oxopropanoate 
• 86-51-1 2,3-dimethyoxybenzaldehyde 
• 91-16-7 1,2-dimethoxybenzene 
• 108-24-7 acetic anhydride 
• 64-19-7 acetic acid 
• 141-78-6 ethyl acetate 

Downstream Products

• 13494-10-5 2',3'-dihydroxyacetophenone 
• 703-98-0 1-(2-hydroxy-3-methoxyphenyl)ethanone 
• 103517-22-2 3-ethyl-1,2-dimethoxybenzene 
• 121704-80-1 2-bromo-2’,3’-dimethoxyacetophenone 
• 93213-66-2 3-Phenyl-1-(2,3-dimethoxy-phenyl)-propandion-(1,3) 
• 23997-79-7 1-(2,3-dimethoxy-phenyl)-ethanone oxime 
• 178551-80-9 3-(3,4-dichlorophenyl)-1-(3,4-dimethoxyphenyl)propenone 
• 321525-46-6 3-(3,4-dichlorophenyl)-5,6-dimethoxyindan-1-one 
• 2134-91-0 4-hydroxy-5-methoxyisophthalic acid 
• 34809-90-0 3-acetyl-4-hydroxy-3-methoxybenzaldehyde 

Relevant academic research and scientific papers

TRPML MODULATORS

The present invention provides compounds, pharmaceutically acceptable compositions thereof, and methods of using the same.

Extensive structure modification on luteolin-cinnamic acid conjugates leading to BACE1 inhibitors with optimal pharmacological properties

BACE1 inhibitory conjugates derived from two natural products, luteolin (1) and p-hydroxy-cinnamic acid (2), were subjected to systematic structure modifications, including various positions in luteolin segment for conjugation, different linkers (length, bond variation), as well as various substitutions in cinnamic acid segment (various substituents on benzene, and replacement of benzene by heteroaromatics and cycloalkane). Optimal conjugates such as 7c and 7k were chosen on the basis of a series of bioassay data for further investigation.

Solvent Dependence of the Monomer–Dimer Equilibrium of Ketone-Substituted Triscatecholate Titanium(IV) Complexes

Hierarchical helicates based on ketone-substituted titanium(IV)triscatecholates show different monomer-dimer behavior depending on different solvents. The dimerization constants of a whole series of differently alkyl-substituted complexes is analyzed to show that the solvent has a very strong influence on the dimerization. Hereby, effects like solvophobicity/philicity, sterics, electronics of the substituents and weak side-chain—side-chain interactions seem to act in concert.

Iridium-Catalyzed C(sp3)?H Addition of Methyl Ethers across Intramolecular Carbon–Carbon Double Bonds Giving 2,3-Dihydrobenzofurans

Intramolecular addition of an O-methyl C(sp3)?H bond across a carbon-carbon double bond occurs in the iridium-catalyzed reaction of methyl 2-(propen-2-yl)phenyl ethers. The Ir/(S)-DTBM-SEGPHOS catalyst promotes the reaction efficiently in toluene at 110–135 °C to afford 3,3-dimethyl-2,3-dihydrobenzofurans. Enantioselective C(sp3)?H addition is achieved in the reaction of methyl 2-(1-siloxyethenyl)phenyl ethers, affording enantioenriched 3-hydroxy-2,3-dihydrobenzofuran derivatives with up to 96% ee. (Figure presented.).

SYNTHESIS AND ANTICANCER ACTIVITY OF ARYL AND HETEROARYL-QUINOLIN DERIVATIVES

A compound of Formula I is disclosed as follows: or a pharmaceutically acceptable salt, prodrug, solvate, or metabolite thereof, wherein R is hydrogen, P(═O)(OH)2, P(═O)(O(C1-C18)alkylene(C6-C20)aryl)2, P(═O)(OH)(OM), P(═O)(OM)2, P═O(O2M), S(═O)(OH)2, S(═O)(O(C1-C18)alkylene(C6-C20)aryl)2, S(═O)(OH)(OM), S(═O)(OM)2; M is a monovalent or divalent metal ion, or alkylammonium ion; W is (C6-C20)aryl, (C6-C20)heteroaryl, (C1-C18)alkyl(C6-C20)aryl, (C1-C18)alkyl(C6-C20)heteroaryl, hydroxy(C6-C20)aryl, hydroxy(C6-C20)heteroaryl, (C1-C18)alkoxy(C6-C20)aryl, (C1-C18)alkoxy(C6-C20)heteroaryl, (C1-C18)alkylenedioxy(C6-C20)aryl, (C1-C18)alkylenedioxy(C6-C20)heteroaryl, halo(C6-C20)aryl, halo(C6-C20)heteroaryl, (C1-C18)alkylamino(C6-C20)aryl, (C1-C18)alkylamino(C6-C20)heteroaryl, (C1-C18)cycloalkylamino(C6-C20)aryl, or (C1-C18)cycloalkylamino(C6-C20)heteroaryl, and their OR8 substutes; R5 is (C1-C18alkoxy, hydrogen, hydroxyl, O—(C1-C18)alkyl(C6-C20)aryl, halo or OR8, or R5 and R6 are (C1-C18)dioxy provided that R7 is hydrogen; R6 is hydroxyl, O—(C1-C18)alkyl(C6-C20)aryl, halo or ORR, (C1-C18)alkoxy, (C1-C18)alkylamino, or (C1-C18)cycloalkylamino, or R6 and R7 are (C1-C18)dioxy provided that R5 is hydrogen; R7 is hydrogen, halo or OR8, hydroxyl, or O—(C1-C18)alkyl(C6-C20)aryl; and R8 is P(═O)(OH)2, P(═O)(O(C1-C18)alkyl(C6-C20)aryl)2, P(═O)(OH)(OM), or P(═O)(OM)2, P═O(O2M).

Highly selective vapor-phase acylation of veratrole over H3PO4/TiO2-ZrO2: Using ethyl acetate as a green and efficient acylating agent

A simple sol-gel method with and without surfactant was applied to prepare TiO2-ZrO2 mixed oxides containing Ti and Zr at a molar ratio of 1:1. Several catalysts containing w=15%-35% H3PO4 were set up using these mixed oxides. The physical and chemical properties of catalysts were investigated by BET, SEM and pyridine adsorption-desorption. The catalytic performance of each material was determined for the vapor-phase acylation of veratrole (1,2-dimethoxybenzene) to 3,4-dimethoxyacetophenone (3,4-DMAP), which was found to be the major product of the reaction of veratrole with ethyl acetate, with alkylated products being the minor products. 2,3-Dimethoxyacetophenone (2,3-DMAP) was not detected in the product stream. In the best experimental conditions, the alkylated products were less than 0.7%. This reaction may represent an environmentally friendly alternative to use the ethyl acetate as the acylating reagent. The feed molar ratios of veratrole/ethyl acetate were varied over a wide range of 0.1 to 1, and the optimum feed ratio of veratrole/ethyl acetate was 1:3. Space velocity employed in the veratrole acylation reported as WHSV (veratrole) was 1.2 h-1. The acylation reactions were carried out in the temperature range of 423 to 673 and the optimum H3PO4 content for acylation was w15%.

Preparative monohydroxyflavanone syntheses and a protocol for gas chromatography-mass spectrometry analysis of monohydroxyflavanones

We describe a facile efficient, and preparative approach for monohydroxyflavanone syntheses. Using this protocol, a hydroxyl is regio-selectively introduced at one carbon of a flavanone A- or B-ring per synthesis. The seven possible isomers were each synthesized from the corresponding monomethoxymethoxylated 2′-hydroxychalcones in acidic solution. These monohydroxyflavanones were characterized using a gas chromatography-mass spectrometry (GC-MS) system that incorporated a DB-5 capillary column. Ours is the first report of a preparative synthetic method during which a single hydroxyl can be selectively added to a flavanone A- or B-ring at any position. We are also the first to develop a procedure that separates the seven isomers by GC and characterizes the mass spectra of the isomers. Both the synthetic method and the GC-MS conditions may become important tools during future flavanone metabolism and oxidation studies.

Hierarchical assembly of helicate-type dinuclear titanium(IV) complexes

The ligands 4-7-H2 were used in coordination studies with titanium(IV) and gallium(III) ions to obtain dimeric complexes Li 4[(4-7)6Ti2] and Li6[(4/5a) 6Ga2]. The X-ray crystal structures of Li 4[(4)6Ti2], Li4[(5b) 6Ti2], and Li4[(7a)6Ti2] could be obtained. While these complexes are triply lithium-bridged dimers in the solid state, a monomer/dimer equilibrium is observed in solution by NMR spectroscopy and ESI FT-ICR MS. The stability of the dimer is enhanced by high negative charges (Ti(IV) versus Ga(III)) of the monomers, when the carbonyl units are good donors (aldehydes versus ketones and esters), when the solvent does not efficiently solvate the bridging lithium ions (DMSO versus acetone), and when sterical hindrance is minimized (methyl versus primary and secondary carbon substituents). The dimer is thermodynamically favored by enthalpy as well as entropy. ESI FT-ICR mass spectrometry provides detailed insight into the mechanisms with which monomeric triscatecholate complexes as well as single catechol ligands exchange in the dimers. Tandem mass spectrometric experiments in the gas phase show the dimers to decompose either in a symmetric (Ti) or in an unsymmetric (Ga) fashion when collisionally activated. The differences between the Ti and Ga complexes can be attributed to different electronic properties and a charge-controlled reactivity of the ions in the gas phase. The complexes represent an excellent example for hierarchical self-assembly, in which two different noncovalent interactions of well balanced strengths bring together eleven individual components into one well-defined aggregate.

Benzopyran derivatives having leukotriene-antagonistic action

The present invention relates to novel 4-oxo-4H-1-benzopyran compounds containing benzyloxymethyl, 3-phenylpropyl, or other araliphatic substituents in their 8-position. These compounds show a leukotriene-antagonistic activity. The compounds are characterized by good oral adsorption. The compounds of the present invention may be used as anti-inflammatory and antiallergic medicaments, and in the treatment of cardiovascular diseases.