35322-20-4

Usage

Uses

Used in Pharmaceutical Synthesis:
4-(4-Methoxy-phenyl)-2,4-dioxo-butyric acid methyl ester is utilized as a key intermediate in the production of various pharmaceuticals, contributing to the development of new drugs and therapeutic agents.
Used in Organic Compounds Synthesis:
In the field of organic chemistry, 4-(4-METHOXY-PHENYL)-2,4-DIOXO-BUTYRIC ACID METHYL ESTER is employed as a building block for synthesizing a range of organic compounds, enhancing the diversity and complexity of chemical structures that can be created.
Used in Research and Development:
4-(4-Methoxy-phenyl)-2,4-dioxo-butyric acid methyl ester is used as a subject of study in research and development, where its structural and functional properties are explored for potential applications in various scientific and industrial domains.
Used in Chemical Education:
4-(4-METHOXY-PHENYL)-2,4-DIOXO-BUTYRIC ACID METHYL ESTER may also be used in educational settings to illustrate the principles of organic synthesis and the properties of specific functional groups, providing a practical example for students to understand the synthesis of complex molecules.

InChI:InChI=1/C13H14O5/c1-3-18-13(16)12(15)8-11(14)9-4-6-10(17-2)7-5-9/h4-7H,3,8H2,1-2H3

Upstream product

• 64-17-5 ethanol 
• 95-92-1 oxalic acid diethyl ester 
• 100-06-1 1-(4-methoxyphenyl)ethanone 
• 3319-15-1 rac-1-(4-methoxyphenyl)-ethanol 
• 123-11-5 4-methoxy-benzaldehyde 

Downstream Products

• 129227-33-4 4-(4-Methoxy-phenyl)-4-oxo-2-[(3-oxo-3,4-dihydro-quinoxalin-2-yl)-hydrazono]-butyric acid ethyl ester 
• 83715-77-9 6-[2-(4-Methoxy-phenyl)-2-oxo-ethyl]-2-methyl-3-thioxo-3,4-dihydro-2H-[1,2,4]triazin-5-one 
• 112100-23-9 7-<3'-carboethoxy-5'-(p-methoxyphenyl)pyrazolyl>-3-<2-oxo-2-(p-methoxyphenyl)ethyl>-4H-as-triazino<3,4-a>phthalizin-4-one 
• 112080-18-9 C₃₄H₃₀N₆O₆ 
• 83715-74-6 6-[2-(4-Methoxy-phenyl)-2-oxo-ethyl]-3-methylsulfanyl-4H-[1,2,4]triazin-5-one 
• 89569-82-4 3-Mercapto-6-[2-(4-methoxy-phenyl)-2-oxo-ethyl]-2H-[1,2,4]triazin-5-one 
• 938182-54-8 ethyl 5-(4-methoxyphenyl)-1H-pyrazole-3-carboxylate 
• 55558-77-5 4-(4-methoxyphenyl)-2,4-dioxobutanoic acid 
• 938182-54-8 ethyl 5-(4-methoxyphenyl)-1H-pyrazole-3-carboxylate 
• 83715-68-8 6-(4-Methoxy-phenyl)-2-methyl-2H-thieno[2,3-e][1,2,4]triazine-3-thione 
• 83715-62-2 6-(4-Methoxy-phenyl)-3-piperidin-1-yl-thieno[2,3-e][1,2,4]triazine 
• 83715-59-7 6-(4-Methoxy-phenyl)-3-morpholin-4-yl-thieno[2,3-e][1,2,4]triazine 
• 618070-51-2 ethyl 3-(4-methoxyphenyl)-1-methyl-1H-pyrazole-5-carboxylate 
• 852816-12-7 ethyl 1-methyl-5-[4-(methyloxy)phenyl]-1H-pyrazole-3-carboxylate 

Relevant academic research and scientific papers

Synthesis and biological evaluation of chalcone-linked pyrazolo[1,5-: A] pyrimidines as potential anticancer agents

A series of pyrazolo[1,5-a]pyrimidines substituted at C5 with 1-phenylprop-2-en-1-one (6a-q) and 3-phenylprop-2-en-1-one (7a-k) was synthesized and evaluated for antiproliferative activity. Among them, 6h was found to be the most active compound against the MDA-MB-231 cell line with an IC50 of 2.6 μM. The antiproliferative activity of this series of compounds ranged from 2.6 to 34.9 μM against A549 (lung cancer), MDA-MB-231 (breast cancer) and DU-145 (prostate cancer) cell lines. FACS analysis revealed that these hybrids arrest the cell cycle at the subG1 phase. Western blot analysis and an immunofluorescence assay showed the inhibition of the EGFR and STAT3 axis, which plays an important role in cell survival and apoptosis. Western blot and RT-PCR analyses that displayed an increase in apoptotic proteins such as p53, p21 and Bax and a decrease in the anti-apoptotic proteins Bcl-2 and procaspase-9 confirmed the ability of these hybrids to trigger cell death by apoptosis. Molecular docking studies described the binding of these hybrids to the ATP binding site of EGFR.

Lewis acid-promoted synthesis of highly substituted pyrrole-fused benzoxazinones and quinoxalinones

A synthesis of a series of novel fused tricyclic heterocyclic compounds has been achieved in one-pot reaction set up starting from (E)-3-(2-oxo-2-phenylethylidene)indolin-2-one and 1,4-benzoxazinone/quinoxalinone derivatives promoted by tin(IV) chloride.

A new synthetic approach for pyrazolo[1,5-a]pyrazine-4(5H)-one derivatives and their antiproliferative effects on lung adenocarcinoma cell line

Abstract: Starting from the 3,5-dimethyl pyrazole ring and acetophenone derivatives, five different N-propargylated C-3 substituted pyrazoles were obtained. These derivatives were reacted with different amine derivatives using Cs2CO3 in methanol and 11 different pyrazolo [1,5-a] pyrazine-4(5H)-one derivatives were obtained, which are not found in the literature. The cytotoxic effects of these derivatives in the A549 cell line were investigated. The 160?μM concentration of two derivatives was found to increase cell death rate to 50%, and two derivatives increased cell death rate by up to 40%. The structure–activity relationship (SAR) study revealed an amide group with a long alkyl chain and benzene ring with a p-CF3 group could be important for efficiency. With theoretical ADMET studies of pyrazolopyrazine derivatives, pharmacokinetic phases were predicted to be suitable. Graphic abstract: [Figure not available: see fulltext.].

Synthesis, in vitro anticancer activity and in silico studies of certain isoxazole-based carboxamides, ureates, and hydrazones as potential inhibitors of VEGFR2

The ensuing research presents the results of in vitro anticancer activity of novel 28 compounds of isoxazole–based carboxamides 3(a-d); ureates 4(a-g), 5, 6, 7a,b, 8; and hydrazones 9(a-f), 10(a-d), 11a,b as potential inhibitors of VEGFR2. The carboxamide

Design and synthesis of novel 5-arylisoxazole-1,3,4-thiadiazole hybrids as α-glucosidase inhibitors

Background: α-Glucosidase inhibitors have occupied a significant position in the treatment of type 2 diabetes. In this respect, the development of novel and efficient non-sugar-based inhibitors is in high demand. Objective: Design and synthesis of new 5-arylisoxazole-1,3,4-thiadiazole hybrids possessing α-glucosidase inhibitory activity were developed. Methods: Different derivatives were synthesized by the reaction of various 5-arylisoxazole-3-carboxylic acids and ethyl 2-((5-amino-1,3,4-thiadiazol-2-yl)thio)acetate. Finally, they were evalu-ated for their α-glucosidase inhibitory activity. Results: It was found that ethyl 2-((5-(5-(2-chlorophenyl)isoxazole-3-carboxamido)-1,3,4-thiadiazol-2-yl)thio)acetate (5j) was the most potent compound (IC50 = 180.1 μM) compared with acarbose as the reference drug (IC50 = 750.0 μM). Also, the kinetic study of 5j revealed a competitive inhibition and docking study results indicated desired interactions of that compound with amino acid residues located close to the active site of α-glucosidase. Conclusion: Good α-glucosidase inhibitory activity obtained by the title compounds introduced them as an efficient scaffold, which merits to be considered in anti-diabetic drug discovery developments.

Design and Synthesis of Novel Arylisoxazole-Chromenone Carboxamides: Investigation of Biological Activities Associated with Alzheimer's Disease

A novel series of hybrid arylisoxazole-chromenone carboxamides were designed, synthesized, and evaluated for their cholinesterase (ChE) inhibitory activity based on the modified Ellman's method. Among synthesized compounds, 5-(3-nitrophenyl)-N-{4-[(2-oxo-

Green and efficient synthesis of new pyrido[2,3-d]pyrimidine derivatives using Pd/SBA-15 as a nanocatalyst

N-Fused heterocycles have received significant attention over the years as valuable compounds due to their biological and pharmaceutical activities. Heterogeneous catalysts such as periodic mesoporous materials have played an important role in the synthes

Novel hybrid molecules of isoxazole chalcone derivatives: Synthesis and study of In Vitro cytotoxic activities

Background: Now-a-days, the model of “hybrid drugs” has acquired recognition in medicine due to their significant role in the treatment of different health problems. Methods: We have synthesized new series of isoxazole-chalcone conjugates (14a-m) by the C

Design, synthesis and structure-based optimization of novel isoxazole-containing benzamide derivatives as FtsZ modulators

Antibiotic resistance among clinically significant bacterial pathogens is becoming a prevalent threat to public health, and new antibacterial agents with novel mechanisms of action hence are in an urgent need. Utilizing computational docking method and structure-based optimization strategy, we rationally designed and synthesized two series of isoxazol-3-yl- and isoxazol-5-yl-containing benzamide derivatives that targeted the bacterial cell division protein FtsZ. Evaluation of their activity against a panel of Gram-positive and -negative pathogens revealed that compounds B14 and B16 that possessed the isoxazol-5-yl group showed strong antibacterial activity against various testing strains, including methicillin-resistant Staphylococcus aureus and penicillin-resistant S. aureus. Further molecular biological studies and docking analyses proved that the compound functioned as an effective inhibitor to alter the dynamics of FtsZ self-polymerization via a stimulatory mechanism, which finally terminated the cell division and caused cell death. Taken together, these results could suggest a promising chemotype for development of new FtsZ-targeting bactericidal agent.

Synthesis and cellular bioactivities of novel isoxazole derivatives incorporating an arylpiperazine moiety as anticancer agents

In our endeavour towards the development of effective anticancer therapeutics, a novel series of isoxazole-piperazine hybrids were synthesized and evaluated for their cytotoxic activities against human liver (Huh7 and Mahlavu) and breast (MCF-7) cancer ce