60946-77-2

Basic information

• Product Name: 3-(2,4-DIMETHOXY-PHENYL)-3-OXO-PROPIONIC ACID ETHYL ESTER
• Synonyms: ETHYL (2,4-DIMETHOXYBENZOYL)ACETATE;3-(2,4-DIMETHOXY-PHENYL)-3-OXO-PROPIONIC ACID ETHYL ESTER;3-(2,4-DIMETHOXYPHENYL)-3-OXOPROPANOIC ACID ETHYL ESTER
• CAS NO: 60946-77-2
• Molecular Formula: C₁₃H₁₆O₅
• Molecular Weight: 252.26
• Mol File: 60946-77-2.mol

Chemical Properties

• Appearance: /
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 3-(2,4-DIMETHOXY-PHENYL)-3-OXO-PROPIONIC ACID ETHYL ESTER(CAS DataBase Reference)
• NIST Chemistry Reference: 3-(2,4-DIMETHOXY-PHENYL)-3-OXO-PROPIONIC ACID ETHYL ESTER(60946-77-2)
• EPA Substance Registry System: 3-(2,4-DIMETHOXY-PHENYL)-3-OXO-PROPIONIC ACID ETHYL ESTER(60946-77-2)

Safety Data

• Hazardous Substances Data: 60946-77-2(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
3-(2,4-DIMETHOXY-PHENYL)-3-OXO-PROPIONIC ACID ETHYL ESTER is utilized as an intermediate in the synthesis of a range of drugs. Its unique structure and reactivity make it a valuable component in the development of new medicinal compounds, contributing to the advancement of pharmaceutical formulations and treatments.
Used in Organic Synthesis:
In the realm of organic synthesis, 3-(2,4-DIMETHOXY-PHENYL)-3-OXO-PROPIONIC ACID ETHYL ESTER is employed as a key building block. Its versatility in chemical reactions allows for the construction of complex organic molecules, facilitating the discovery and production of novel chemical compounds with potential applications across various industries.

Upstream product

• 39828-35-8 2,4-dimethoxybenzoyl chloride 
• 6148-64-7 ethyl potassium malonate 
• 829-20-9 2',4'-dimethoxyacetophenone 
• 105-58-8 Diethyl carbonate 

Downstream Products

• 1435467-42-7 1-(2-aminoethyl)-6-(2,4-dimethoxyphenyl)-2-thioxo-2,3-dihydropyrimidin-4(1H)-one hydrochloride 
• 1435469-83-2 6-(2,4-dimethoxyphenyl)-1-(2-isopropoxyethyl)-2-thioxo-2,3-dihydropyrimidin-4(1H)-one 
• 1435467-41-6 tert-butyl 2-(6-(2,4-dimethoxyphenyl)-4-oxo-2-thioxo-3,4-dihydropyrimidin-1(2H)-yl)ethylcarbamate 
• 23982-47-0 3-(2,4-dimethoxyphenyl)isoxazol-5(4H)-one 
• 796089-78-6 coumestrol 

Relevant articles and documents

Identification of Novel Coumestan Derivatives as Polyketide Synthase 13 Inhibitors against Mycobacterium tuberculosis

Inhibition of the mycolic acid pathway has proven a viable strategy in antitubercular drug discovery. The AccA3/AccD4/FadD32/Pks13 complex of Mycobacterium tuberculosis constitutes an essential biosynthetic mechanism for mycolic acids. Small molecules targeting the thioesterase domain of Pks13 have been reported, including a benzofuran-based compound whose X-ray cocrystal structure has been very recently solved. Its initial inactivity in a serum inhibition titration (SIT) assay led us to further probe other structurally related benzofurans with the aim to improve their potency and bioavailability. Herein, we report our preliminary structure-activity relationship studies around this scaffold, highlighting a natural product-inspired cyclization strategy to form coumestans that are shown to be active in SIT. Whole genome deep sequencing of the coumestan-resistant mutants confirmed a single nucleotide polymorphism in the pks13 gene responsible for the resistance phenotype, demonstrating the druggability of this target for the development of new antitubercular agents.

White mulberry root-bark active ingredient Morusin derivative and application and preparation method thereof

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Application and preparation method of Morusignin L and derivatives thereof

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Opening or closing the lock? when reactivity is the key to biological activity

Thiol-mediated processes play a key role to induce or inhibit inflammation proteins. Tailoring the reactivity of electrophiles can enhance the selectivity to address only certain surface cysteines. Fourteen 2',3,4,4'- tetramethoxychalcones with different α-X substituents (X=H, F, Cl, Br, I, CN, Me, p-NO2-C6H4, Ph, p-OMe-C 6H4, NO2, CF3, COOEt, COOH) were synthesized, containing the potentially electrophilic α,β-unsaturated carbonyl unit. The assessment of their reactivity as electrophiles in thia-Michael additions with cysteamine shows a change in the reactivity of more than six orders of magnitude. Moreover, a clear correlation between their reactivity and an influence on the inflammation proteins heme oxygenase-1 (HO-1) and the inducible NO synthase (iNOS) is demonstrated. As the biologically most active compound, the α-CF3-chalcone is shown to inhibit the NO production in RAW264.7 mouse macrophages in the nanomolar range. More than a million by only one substituent: The direct manipulation of the chemical reactivity of electrophilic agents could be proven for chalcones by simply exchanging the α-hydrogen atom of the α,β-unsaturated carbonyl unit with different substituents (X), leading to a change in reactivity of more than six orders of magnitude for thia-Michael additions with cysteamine, which correlates very well with two electrophile-sensitive biological readouts (see scheme).

Design and synthesis of 6,7-methylenedioxy-4-substituted phenylquinolin-2(1H)-one derivatives as novel anticancer agents that induce apoptosis with cell cycle arrest at G2/M phase

Novel 6,7-methylenedioxy-4-substituted phenylquinolin-2(1H)-one derivatives 12a-n were designed and prepared through an intramolecular cyclization reaction and evaluated for in vitro anticancer activity. Among the synthesized compounds, 6,7-methylenedioxy-4-(2,4-dimethoxyphenyl)quinolin-2(1H)-one (12e) displayed potent cytotoxicity against several different tumor cell lines at a sub-micromolar level. Furthermore, results of fluorescence-activated cell sorting (FACS) analysis suggested that 12e induced cell cycle arrest in the G2/M phase accompanied by apoptosis in HL-60 and H460 cells. This action was confirmed by Hoechst staining and caspase-3 activation. Due to their easy synthesis and remarkable biological activities, 4-phenylquinolin-2(1H)-one analogs (4-PQs) are promising new anticancer leads based on the quinoline scaffold. Accordingly, compound 12e was identified as a new lead compound that merits further optimization and development as an anticancer candidate.

Synthesis and herbicidal evaluation of novel 3-[(α-hydroxy- substituted)benzylidene]pyrrolidine-2,4-diones

A series of 3-[(α-hydroxy-substituted) benzylidene]pyrrolidine-2,4- dione derivatives were synthesized as candidate herbicides by reacting different aroyl acetates with N-substituted glycine esters. The new compounds were identified by 1H NMR spectroscopy and elemental analyses. Their herbicidal activities were evaluated. Some compounds exhibited excellent herbicidal activities at a dose of 187.5 g/ha. A suitable electron-donating substituent at the 2- and/or 4-position of the phenyl ring was essential for high herbicidal activity, a result that has not been reported before. It was also found that the title compound's structure-activity relationships were different from those of other similar kinds of earlier compounds, a result that may depend on the enol structure difference.