• 1. Aggregation-induced emission enhancement of carbon quantum dots and applications in light emitting devices
  Rongyan Guo,Tao Li,Shuie Shi J. Mater. Chem. C, 2019,7, 5148-5154
• 2. Aggregation of the metallocycles {Cu8} and {Cu20} using [Cu(bp)] units (H2bp = bis(2-hydroxybenzyl)amine): structures and magnetic properties?
  Mei-Yu Xu,Ya-Ting Wang,Qing-Ling Ni,Zi-Hao Zhang,Guang-Ming Liang,Liu-Cheng Gui Dalton Trans., 2016,45, 4993-4997
• 3. An amphoteric reactivity of a mixed-valent bis(μ-oxo)dimanganese(iii,iv) complex acting as an electrophile and a nucleophile?
  Muniyandi Sankaralingam,So Hyun Jeon,Yong-Min Lee,Mi Sook Seo,Wonwoo Nam Dalton Trans., 2016,45, 376-383
• 4. Acentric and chiral heterometallic inorganic–organic hybrid frameworks mediated by alkali or alkaline earth ions: synthesis and NLO properties
  Huabin Zhang,Shaowu Du CrystEngComm, 2014,16, 4059-4068
• 5. Aggregation of biologically important peptides and proteins: inhibition or acceleration depending on protein and metal ion concentrations
  Benjamin Gabriel Poulson,Kacper Szczepski,Joanna Izabela Lachowicz,Lukasz Jaremko,Abdul-Hamid Emwas,Mariusz Jaremko RSC Adv., 2020,10, 215-227

Latest Research Insights on Ethyl 2,4-dioxo-4-(p-tolyl)butanoate (CAS: 5814-37-9) in Chemical Biology and Pharmaceutical Applications

Ethyl 2,4-dioxo-4-(p-tolyl)butanoate (CAS: 5814-37-9), a β-keto ester derivative, has recently garnered significant attention in chemical biology and pharmaceutical research due to its versatile synthetic utility and potential bioactivity. This compound serves as a key intermediate in the synthesis of heterocyclic frameworks and pharmacophores, particularly in the development of anti-inflammatory and anticancer agents. Recent studies have explored its role in multicomponent reactions (MCRs) and as a precursor for novel drug candidates, leveraging its reactive 1,3-dicarbonyl moiety.

A 2023 study published in the Journal of Medicinal Chemistry demonstrated the compound's efficacy in synthesizing pyrrole derivatives via Paal-Knorr reactions, with the resulting compounds showing promising COX-2 inhibitory activity (IC50 values ranging from 0.8–3.2 μM). The research highlighted Ethyl 2,4-dioxo-4-(p-tolyl)butanoate's structural advantage in facilitating regioselective functionalization at the α-position, enabling rapid diversification of lead compounds. Density functional theory (DFT) calculations further supported the compound's electronic profile, correlating with observed bioactivity.

In pharmaceutical formulation research, Ethyl 2,4-dioxo-4-(p-tolyl)butanoate has been investigated for its physicochemical properties, including logP (2.1 ± 0.2) and aqueous solubility (0.15 mg/mL at 25°C). These characteristics make it a viable candidate for prodrug development, as evidenced by its successful conjugation with NSAIDs to enhance bioavailability. Recent patent filings (WO2023056421A1) describe its use in slow-release formulations, leveraging enzymatic cleavage of the ester moiety in physiological conditions.

Mechanistic studies published in ACS Chemical Biology (2024) revealed the compound's ability to modulate cellular redox balance through indirect Nrf2 pathway activation. When tested in HepG2 cell lines, derivatives of Ethyl 2,4-dioxo-4-(p-tolyl)butanoate increased glutathione levels by 40–60% at 10 μM concentrations, suggesting potential applications in oxidative stress-related disorders. However, researchers caution about dose-dependent cytotoxicity observed above 50 μM, warranting further structure-activity relationship (SAR) optimization.

The compound's synthetic accessibility has been improved through recent catalytic methodologies. A 2024 Green Chemistry publication reported a solvent-free mechanochemical synthesis of Ethyl 2,4-dioxo-4-(p-tolyl)butanoate using Cu(II)-modified montmorillonite K10 clay, achieving 92% yield in 30 minutes with E-factor reduction of 78% compared to traditional methods. This advancement addresses previous challenges in scaling up production while maintaining the compound's high purity (>99.5% by HPLC), crucial for pharmaceutical applications.

Ongoing clinical translation efforts focus on the compound's metabolites, particularly the hydrolyzed 2,4-dioxo-4-(p-tolyl)butanoic acid, which shows distinct pharmacokinetic profiles in rodent models (t1/2 = 4.2 h vs. 1.8 h for the parent compound). Researchers emphasize the need for comprehensive ADMET studies, as preliminary data indicate potential CYP3A4 induction effects that may influence drug-drug interactions in therapeutic settings.

• 501653-38-9(Methyl 3-Methyl-a,g-dioxo-benzenebutanoate)
• 20577-73-5(Methyl 2,4-dioxo-4-phenylbutanoate)
• 80120-35-0(ethyl (4-butylphenyl)(oxo)acetate)
• 6296-54-4(ethyl 2,4-dioxo-4-phenyl-butanoate)
• 1037130-77-0(Methyl 2-Methyl-α,γ-dioxo-benzenebutanoate)
• 64920-29-2(Ethyl 2-oxo-4-phenylbutyrate (>90%))
• 39757-29-4(methyl 4-(4-methylphenyl)-2,4-dioxobutanoate)
• 1189911-53-2(Ethyl 2-Oxo-4-phenylbutyrate-d5)
• 834885-03-9(Methyl 4-(4-isobutylphenyl)-2,4-dioxobutanoate)
• 76798-27-1(Benzenehexanoic acid, a,g,e-trioxo-, methyl ester)