2944-49-2

Usage

Uses

Used in Pharmaceutical Industry:
2,3-Dimethylanisole is used as a starting reagent for the synthesis of biphenyl-indanone A, which is a positive allosteric modulator of the metabotropic glutamate receptor subtype 2. This application is significant due to its potential role in the development of novel treatments for neurological and psychiatric disorders.
Additionally, 2,3-Dimethylanisole can be used to produce 2-methoxy-6-methyl-benzaldehyde by heating, which may have further applications in the synthesis of various organic compounds and specialty chemicals.

InChI:InChI=1/C9H12O/c1-7-5-4-6-9(10-3)8(7)2/h4-6H,1-3H3

Upstream product

• 526-75-0 2,3-Dimethylphenol 
• 562-54-9 potassium methyl sulfate 
• 77-78-1 dimethyl sulfate 
• 74-88-4 methyl iodide 
• 616-38-6 carbonic acid dimethyl ester 
• 17938-69-1 4-iodo-2,3-dimethyl-phenol 

Downstream Products

• 854677-72-8 4-(4-methoxy-2,3-dimethyl-phenyl)-4-oxo-butyric acid 
• 526-75-0 2,3-Dimethylphenol 
• 14963-97-4 3-methoxyphthalic acid 
• 81029-03-0 4-Methoxy-2,3-dimethylnitrobenzene 
• 854636-88-7 toluene-4-sulfonic acid-[2-(4-methoxy-2,3-dimethyl-benzoyl)-anilide] 
• 38998-17-3 2,3-dimethyl-4-methoxybenzaldehyde 
• 25347-66-4 4,4'-Dimethoxy-2,2',3,3'-tetramethyl-stilben 
• 61808-02-4 2,3-dimethyl-phenetole 
• 124267-93-2 3-Methyl-2-propylphenetole 
• 124267-92-1 2-Methyl-3-propylphenetole 
• 124268-41-3 2-Ethyl-3-propylphenetole 
• 124267-91-0 3-Methyl-2-ethylphenetole 
• 124267-94-3 2,3-Dipropylphenetole 
• 118104-43-1 7,8-dimethyl-6-methoxy-1,2,3,4,4a,9a-hexahydrofluoren-9-one 

Relevant academic research and scientific papers

Impact of N-Alkylamino Substituents on Serotonin Receptor (5-HTR) Affinity and Phosphodiesterase 10A (PDE10A) Inhibition of Isoindole-1,3-dione Derivatives

In this study, a series of compounds derived from 4-methoxy-1H-isoindole-1,3(2H)-dione, potential ligands of phosphodiesterase 10A and serotonin receptors, were investigated as potential antipsychotics. A library of 4-methoxy-1H-isoindole-1,3(2H)-dione derivatives with various amine moieties was synthesized and examined for their phosphodiesterase 10A (PDE10A)-inhibiting properties and their 5-HT1A and 5-HT7 receptor affinities. Based on in vitro studies, the most potent compound, 18 (2-[4-(1H-benzimidazol-2-yl)butyl]-4-methoxy-1H-isoindole-1,3(2H)-dione), was selected and its safety in vitro was evaluated. In order to explain the binding mode of compound 18 in the active site of the PDE10A enzyme and describe the molecular interactions responsible for its inhibition, computer-aided docking studies were performed. The potential antipsychotic properties of compound 18 in a behavioral model of schizophrenia were also investigated.

A Spiroalkylation Method for the Stereoselective Construction of α-Quaternary Carbons and Its Application to the Total Synthesis of (R)-Puraquinonic Acid

Cyclic α-quaternary carbon stereocenters were prepared from biselectrophillic substrates and an easily prepared chiral bicyclic sulfonyl lactam. This was achieved in two steps by spiroalkylation, employing biphasic reaction conditions with a phase-transfer catalyst, followed by reduction and alkylation with a series of alkyl halide electrophiles. The products of this method were isolated in good yields with with high levels of diastereoselectivity. This methodology was employed in the enantioselective total synthesis of (R)-puraquinonic acid (1) for a late-stage installation of the α-quaternary carbon stereocenter. This enabled the shortest synthesis of 1 to date, an eight-pot sequence providing an overall yield of 14%.

Design, synthesis and evaluation of a series of 5-methoxy-2,3-naphthalimide derivatives as AcrB inhibitors for the reversal of bacterial resistance

A series of novel 5-methoxy-2,3-naphthalimide derivatives were designed, synthesized and evaluated for their biological activities. In particular, the ability of the compounds to synergize with antimicrobials, to inhibit Nile Red efflux, and to target AcrB was assayed. The results showed that the most of the tested compounds more sensitized the Escherichia coli BW25113 to the antibiotics than the parent compounds 7c and 15, which were able to inhibit Nile Red efflux. Significantly, compound A5 possessed the most potent antibacterial synergizing activity in combination with levofloxacin by 4 times and 16 times at the concentration of 8 and 16 μg/mL, respectively, whilst A5 could effectively abolish Nile Red efflux at 100 μM. Additionally, target effect of A5 was confirmed in the outer- or inner membrane permeabilization assays. Therefore, A5 is an excellent lead compound for further structural optimization.

Synthesis, in vitro cytotoxicity and anti-platelet activity of new 1,3-bentzenedisulfonamides

To obtain more active and selective anti-platelet candidate drugs, we tried to introduce a methyl group at the 5-position and 6-position of the parent benzene ring first time, respectively or simultaneously. The idea could inspect compound with tetra-substituted or penta-substituted characteristics rather than retained classical 1,3,4-position triple substitutions characteristic whether it continues to have anti-platelet activity in vitro. The biological evaluation revealed that most of compounds with this novel structure were more potent than the positive control drug Picotamide. At the concentration of 1.3 μmol/L, using Arachidonic acid as an inducer, it was found that the anti-platelet activity in vitro of five compounds 1a, 1b, 1c, 2f, and 3d was higher than that of Picotamide and the series 1 compounds were generally higher than that of the series 2 and 3. And with ADP as an inducer, the activity in vitro of nine compounds 2a, 2b, 2d, 2f, 2g, 2h, 3a, 3b, and 3c was more elevated than that of Picotamide and the compounds of series 2 and 3 were all evidently even more active than that of series 1. The proportion of newly designed target compounds with active is higher than that of previously developed series of compounds. Based on the in vitro activity results, a preliminary analysis of the structure–activity relationship was deduced. Meanwhile, cytotoxic effects in vitro of 11 target compounds 1b, 1c, 2f, 2a, 2b, 3a, 3b, 3c, 2d, 2g, and 2h on L-929 cells were analyzed, but the data analysis shows that at two concentrations, target compounds have higher effect on L-929 cells than that of control drug Picotamide. The reason or mechanism for obtaining higher in vitro activity and higher cytotoxicity of the target compound under tetra- or penta- substitutions requires further relevant research work before conclusion can be drawn.

From catechol-tocopherol to catechol-hydroquinone polyphenolic antioxidant hybrids

Multidefence antioxidants represent a valuable solution for the protection against oxidative stress. From the planned synthesis of a catechol-tocopherol hybrid, we isolated a catechol-hydroquinone hybrid through a BBr3-mediated benzochromene-fluoren-1-ol transposition. The compound prepared showed a remarkable chain-breaking antioxidant in the catechol portion, while the very sensitive hydroquinone moiety revealed to be an efficient generator of hydroperoxyl radicals.

CXCR3 RECEPTOR AGONISTS

Compounds are provided having the structure of the following Formula I: where R, R1, R2, R3a and R3b are as defined herein. Pharmaceutical compositions comprising such compounds, as well as methods related to their manufacture and use, are also provided.

2. 3 - Naphthalenedicarboxylic acid imide derivative and its preparation method and application (by machine translation)

The invention provides a compound of formula I illustrated compound or isomer thereof or solvates or salts and its preparation method and application, the compounds of the HAUGLAND gram negative bacteria over-expression AcrB has better antibacterial synergistic activity and efflux inhibitory activity. (by machine translation)

Synthetic process of rhein

The invention relates to a synthetic process of rhein. The synthetic process comprises the steps of: adopting 2,3-dimethyl phenol as a raw material, performing methylation and oxidation to obtain 3-methoxy phthalic acid, performing dehydration by using acetic anhydride to obtain acid anhydride, then performing a Friedel-Crafts reaction between the obtained acid anhydride and excess methyl anisoleunder the action of aluminum trichloride to obtain the product, and then conducting cyclization by using sulfuric acid to obtain an intermediate chrysophanol, performing acetylation on the obtained chrysophanol, performing oxidation to obtain diacerein, and finally carrying out deacetylation to synthesize rhein.

Methylation of phenol and its derivatives with dimethyl carbonate in the presence of Mn2(CO)10, W(CO)6, and Co2(CO)8

Aryl methyl ethers were synthesized by reactions of phenol, substituted phenols, and α- and β-naphthols with dimethyl carbonate in the presence of manganese, tungsten, and cobalt carbonyls. Optimal reactant and catalyst ratios and reaction conditions were found to ensure selective formation of aryl methyl ethers.

The Key Role of the Nonchelating Conformation of the Benzylidene Ligand on the Formation and Initiation of Hoveyda-Grubbs Metathesis Catalysts

Experimental studies of Hoveyda-Grubbs metathesis catalysts reveal important consequences of substitution at the 6-position of the chelating benzylidene ligand. The structural modification varies conformational preferences of the ligand that affects its exchange due to the interaction of the coordinating site with the ruthenium center. As a consequence, when typical S-chelated systems are formed as kinetic trans-Cl2 products, for 6-substituted benzylidenes the preference is altered toward direct formation of thermodynamic cis-Cl2 isomers. Activity data and reactions with tricyclohexylphosphine (PCy3) support also a similar scenario for O-chelated complexes, which display fast trans-Cl2?cis-Cl2 equilibrium observed by NMR EXSY studies. The presented conformational model reveals that catalysts, which cannot adopt the optimal nonchelating conformation of benzylidene ligand, initiate through a high-energy associative mechanism.