32711-91-4

Usage

Uses

Used in Organic Synthesis:
4-(4-METHOXY-PHENYL)-3-OXO-BUTYRIC ACID ETHYL ESTER is used as an intermediate in organic synthesis for the production of various chemical compounds. Its unique structure allows it to be a versatile building block in the creation of complex organic molecules.
Used in Pharmaceutical Research:
In the pharmaceutical industry, 4-(4-METHOXY-PHENYL)-3-OXO-BUTYRIC ACID ETHYL ESTER is used as a key component in the development of new drugs. Its properties make it a valuable asset in medicinal chemistry for the synthesis of potential therapeutic agents.
Used in Chemical Research:
4-(4-METHOXY-PHENYL)-3-OXO-BUTYRIC ACID ETHYL ESTER is also utilized in chemical research to study the properties and reactions of ester compounds. This helps scientists to better understand the behavior of similar molecules and their potential applications in various fields.

Upstream product

• 141-78-6 ethyl acetate 
• 619-41-0 4-(bromoacetyl)toluene 
• 103-80-0 phenylacetyl chloride 
• 14062-18-1 ethyl p-methoxyphenylacetate 
• 42201-84-3 1-ethoxy-1-(tert-butyldimethylsilyloxy)ethene 
• 141-97-9 ethyl acetoacetate 
• 104-92-7 1-bromo-4-methoxy-benzene 
• 89186-81-2 1-ethoxy-1,3-bis[(trimethylsilyl)oxy]buta-1,3-diene 
• 64-17-5 ethanol 
• 66696-84-2 5-(1-hydroxy-2-phenylethylidene)-2,2-dimethyl-1,3-dioxane-4,6-dione 
• 104-01-8 4-Methoxyphenylacetic acid 
• 4693-91-8 4-methoxyphenyl-acetic chloride 
• 226956-10-1 5-[2-(4-Methoxy-phenyl)-acetyl]-2,2-dimethyl-[1,3]dioxane-4,6-dione 
• 2033-24-1 cycl-isopropylidene malonate 

Downstream Products

• 221641-09-4 3-(4-methoxybenzyl)-1-phenyl-5-pyrazolone 
• 1159576-82-5 ethyl (2Z)-3-amino-4-(4-methoxyphenyl)but-2-enoate 
• 1359938-21-8 C₂₀H₂₀O₄ 
• 1430414-78-0 6-(4-methoxybenzyl)-2-(benzyloxy)-4-(2-methylcyclohexyloxy)-3-(prop-1-en-2-yl)pyridine 
• 1430414-74-6 6-(4-methoxybenzyl)-2-(benzyloxy)-3-(prop-1-en-2-yl)pyridin-4-ol 
• 1430414-70-2 6-(4-methoxybenzyl)-2-(benzyloxy)-3-(2-hydroxypropan-2-yl)-pyridin-4-ol 
• 1430414-47-3 ethyl 6-(4-methoxybenzyl)-2-(benzyloxy)-4-hydroxynicotinate 
• 1430414-45-1 ethyl 6-(4-methoxybenzyl)-4-hydroxy-2-oxo-1,2-dihydropyridine-3-carboxylate 
• 143467-68-9 2-butoxy-6-(4-methoxybenzyl)-4(3H)-pyrimidinone 

Relevant academic research and scientific papers

Non-metal Lewis acid-catalyzed cross-Claisen condensation for β-keto esters

In this work, we disclose a new catalytic and highly chemoselective cross-Claisen condensation of esters. In the presence of TBSNTf2 as a non-metal Lewis acid, various esters can undergo cross-Claisen condensation to form β-keto esters which are important building blocks. Compared with the traditional Claisen condensation, this process, employing silyl ketene acetals (SKAs) as carbonic nucleophiles to achieve cross-Claisen condensation, requires mild conditions and has good tolerance of functional groups. This journal is

Deconstructing Noncovalent Kelch-like ECH-Associated Protein 1 (Keap1) Inhibitors into Fragments to Reconstruct New Potent Compounds

Targeting the protein-protein interaction (PPI) between nuclear factor erythroid 2-related factor 2 (Nrf2) and Kelch-like ECH-associated protein 1 (Keap1) is a potential therapeutic strategy to control diseases involving oxidative stress. Here, six classes of known small-molecule Keap1-Nrf2 PPI inhibitors were dissected into 77 fragments in a fragment-based deconstruction reconstruction (FBDR) study and tested in four orthogonal assays. This gave 17 fragment hits of which six were shown by X-ray crystallography to bind in the Keap1 Kelch binding pocket. Two hits were merged into compound 8 with a 220-380-fold stronger affinity (Ki = 16 μM) relative to the parent fragments. Systematic optimization resulted in several novel analogues with Ki values of 0.04-0.5 μM, binding modes determined by X-ray crystallography, and enhanced microsomal stability. This demonstrates how FBDR can be used to find new fragment hits, elucidate important ligand-protein interactions, and identify new potent inhibitors of the Keap1-Nrf2 PPI.

Hauser-Heck: Efficient Synthesis of γ-Aryl-β-ketoesters en Route to Substituted Naphthalenes

γ-Aryl-β-ketoesters can be prepared in one step from aryl bromides and bis(trimethylsilyl) enol ethers using catalytic amounts of Pd(dba)2/t-Bu3P and stoichiometric amounts of Bu3SnF. The wide range of γ-(hetero)aryl-β-ketoesters that can be obtained illustrate the scope and limitations of this novel Hauser-Heck combination. γ-Aryl-β-ketoesters with a 1,3-dioxane acetal in the ortho position can easily be transformed into the hydroxy naphthoate in very good yield. Aqueous formic acid at 65 °C provides optimal conditions for this deprotective aromatization.

Bioisosteric replacement of an acylureido moiety attached to an indolin-2-one scaffold with a malonamido or a 2/4-pyridinoylamido moiety produces a selectively potent Aurora-B inhibitor

Bioisosteric replacement of acylureido moiety in 6-acylureido-3- pyrrolylmethylidene-2-oxoindoline derivatives resulted in a series of malonamido derivatives with indolin-2-one scaffold (11-14). Further conformational restrictions of the malonamido moiety led to 2-oxo-1,2-dihydropyridine (21-25) or a 4-oxo-1,4-dihydropyridine derivatives (31-36). 4-Oxo-1,4-dihydropyridine derivatives were more potent Aurora B inhibitors than their 2-oxo-1,2- dihydropyridine counterparts and demonstrated cytotoxicities against A549 and HepG2 cells in the submicromolar range. In A549 cells, 31h decreased phosphorylation of histone H3, triggered polyploidy, induced expression of pro-apoptotic Fas and FasL with subsequent activation of caspase 8, resulting into apoptosis. In a Huh7-xenograft mouse model, 31h demonstrated potent in vivo efficacy with a daily dose of 5 mg/kg.

Novel pyridinone derivatives as non-nucleoside reverse transcriptase inhibitors (NNRTIs) with high potency against NNRTI-resistant HIV-1 strains

Novel 6-substituted-4-cycloalkyloxy-pyridin-2(1H)-ones were synthesized as non-nucleoside reverse transcriptase inhibitors (NNRTIs), and their biological activity was evaluated. Most of the compounds, especially 26 and 22, bearing a 3-isopropyl and 3-iodine group, respectively, exhibited highly potent activity against wild-type HIV-1 strains and those resistant to reverse transcriptase inhibitors (RTIs). The diastereoisomers of 26-trans and 26-cis were synthesized separately and confirmed with HPLC and NOESY spectra. The 26-trans isomers had an activity about 400-fold more potent than that of 26-cis. The pair of 26-trans enantiomers, one of the most potent inhibitors with EC50 of 4 nM and selectivity index (SI) of 75000, was highly effective against a panel of RTIs-resistant strains with single (Y181C and K103N) or double (A17) mutations in reverse transcriptase. The results suggest that these novel pyridinone derivatives have the potential to be further developed as new antiretroviral drugs with improved antiviral efficacy and drug resistance profile.

PYRAZOLE DERIVATIVES, PREPARATION METHOD THEREOF, AND COMPOSITION FOR PREVENTION AND TREATMENT OF OSTEOPOROSIS CONTAINING SAME

The present invention provides pyrazole derivative compounds and pharmaceutically acceptable salts thereof. The compounds of the present invention have an excellent effect of preventing and treating osteoporosis.

Acylation of Meldrum's acid with arylacetic acid imidazolides as a convenient method for the synthesis of 4-aryl-3-oxobutanoates

C-Acylation of Meldrum's acid by (het)arylacetic acids in ethanol in the presence of 1,1′-carbonyldiimidazole leads to ethyl 4-(het)aryl-3- oxobutanoates in high yields.

Modulation of luminescence intensity of lanthanide complexes by photoinduced electron transfer and its application to a long-lived protease probe

Luminescent lanthanide complexes (Tb3+, Eu3+, etc.) have excellent properties for biological applications, including extraordinarily long lifetimes and large Stokes shifts. However, there have been few reports of lanthanide-based functional probes, because of the difficulty in designing suitable complexes with a luminescent on/off switch. Here, we have synthesized a series of complexes which consist of three moieties: a lanthanide chelate, an antenna, and a luminescence off/on switch. The antenna is an aromatic ring which absorbs light and transmits its energy to the metal, and the switch is a benzene derivative with a different HOMO level. If the HOMO level is higher than a certain threshold, the complex emits no luminescence at all, which indicates that the lanthanide luminescence can be modulated by photoinduced electron transfer (PeT) from the switch to the sensitizer. This approach to control lanthanide luminescence makes possible the rational design of functional lanthanide complexes, in which the luminescence property is altered by a biological reaction. To exemplify the utility of our approach to the design of lanthanide complexes with a switch, we have developed a novel protease probe, which undergoes a significant change in luminescence intensity upon enzymatic cleavage of the substrate peptide. This probe, combined with time-resolved measurements, was confirmed in model experiments to be useful for the screening of inhibitors, as well as for clinical diagnosis.

A quantitative structure-activity relationship study of herbicidal analogues of α-hydroxy-substituted 3-benzylidenepyrrolidene-2,4-diones

A series of pyrrolidine-2,4-dione and piperidine-2,4-dione derivatives were prepared and evaluated for their herbicidal activities where some of these compounds exhibited good bioactivity against Echinochloa crus-galli in comparison with sulcotrione. Quan

Efficient activation of zinc: Application of the Blaise reaction to an expedient synthesis of a statin intermediate

Efficient and practical in situ zinc activation was accomplished by treatment with catalytic amount of an organic acid. The protocol was applied successfully to the Blaise reaction of various nitriles. Noteworthy is the excellent Blaise transformation of (S)-4-chloro-3-trimethylsilyloxybutyronitrile (2b) into tert-butyl (S)-6-chloro-5-hydroxy-3-oxohexanoate (1), a key intermediate for the preparation of HMG-CoA reductase inhibitors (statins).