221121-37-5

Usage

Uses

Used in Pharmaceutical Industry:
4-(4-FLUORO-PHENYL)-3-OXO-BUTYRIC ACID ETHYL ESTER is used as a key intermediate in the synthesis of novel pyridinone derivatives. These pyridinone derivatives act as non-nucleoside reverse transcriptase inhibitors (NNRTIs) with high potency against NNRTI-resistant HIV-1 strains, making them valuable in the development of antiretroviral drugs for the treatment of HIV/AIDS.
Additionally, 4-(4-FLUORO-PHENYL)-3-OXO-BUTYRIC ACID ETHYL ESTER is used in the structural evaluation of 2-substituted 5-hydroxyindole 3-carboxylates. These compounds have been identified as potent inhibitors of human 5-lipoxygenase, an enzyme involved in the production of inflammatory mediators. This application highlights the potential of 4-(4-FLUORO-PHENYL)-3-OXO-BUTYRIC ACID ETHYL ESTER in the development of anti-inflammatory drugs for the treatment of various inflammatory conditions.

InChI:InChI=1/C12H13FO3/c1-2-16-12(15)8-11(14)7-9-3-5-10(13)6-4-9/h3-6H,2,7-8H2,1H3

Upstream product

• 6148-64-7 ethyl potassium malonate 
• 221121-30-8 2-(4-fluorophenyl)-1-(1H-imidazol-1-yl)ethan-1-one 
• 2033-24-1 cycl-isopropylidene malonate 
• 64-17-5 ethanol 
• 459-04-1 4-Fluorophenylacetyl chloride 
• 623-73-4 diazoacetic acid ethyl ester 
• 18511-62-1 4-fluorostyrene oxide 
• 42201-84-3 1-ethoxy-1-(tert-butyldimethylsilyloxy)ethene 
• 587-88-2 ethyl 2-(4-fluorophenyl)acetate 
• 405-50-5 p-Fluorophenylacetic acid 
• 1035695-10-3 5-[2-(4-fluorophenyl)-1-hydroxyethylidene]-2,2-dimethyl-1,3-dioxane-4,6-dione 

Downstream Products

• 1052114-80-3 ethyl 5-(4-fluorophenyl)-4-oxo-1,4-dihydropyridine-3-carboxylate 
• 1052114-81-4 5-(4-fluorophenyl)-4-oxo-1,4-dihydropyridin-3-ylcarboxylic acid 
• 1345855-14-2 N-(2,5-difluoro-4-(3-(1-methyl-1H-pyrazol-4-yl)pyridin-4-yloxy)phenyl)-5-(4-fluorophenyl)-1-methyl-4-oxo-1,4-dihydropyridine-3-carboxamide 
• 1052114-86-9 5-(4-fluorophenyl)-1-methyl-4-oxo-1,4-dihydropyridine-3-carboxylic acid 
• 1345855-04-0 ethyl 5-(4-fluorophenyl )-1-methyl-4-oxo-1,4-dihydropyridine-3-carboxylate 
• 1345855-21-1 N-(4-(2-amino-3-(1-methyl-1H-pyrazol-4-yl)pyridin-4-yloxy)-2,5-difluorophenyl)-5-(4-fluorophenyl)-1-methyl-4-oxo-1,4-dihydropyridine-3-carboxamide 
• 1345855-20-0 N-(4-(2-[bis[(1,1-dimethylethoxy)carbonyl]amino]-3-(1-methyl-1H-pyrazol-4-yl)pyridin-4-yloxy)-2,5-difluorophenyl)-5-(4-fluorophenyl)-1-methyl-4-oxo-1,4-dihydropyridine-3-carboxamide 
• 894802-96-1 7-amino-4-(4-fluoro-benzyl)-1H-quinolin-2-one 
• 221121-54-6 6-(4-fluoro-benzyl)-2-thioxo-2,3-dihydro-1H-pyrimidin-4-one 
• 603999-25-3 ethyl (2Z)-3-amino-4-(4-fluorophenyl)-2-butenoate 
• 1323111-28-9 6-(4-fluorobenzyl)-7H-benzo[f]pyrido[1,2-b][2,7]naphthyridin-7-one 
• 1449300-94-0 1-[2-(dimethylamino)-2-oxoethyl]-5-(4-fluorophenyl)-4-oxo-1,4-dihydropyridine-3-carboxylic acid 

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

Discovery of pyrrolo[2,3-d]pyrimidine derivatives as potent Axl inhibitors: Design, synthesis and biological evaluation

Axl has emerged as an attractive target for cancer therapy due to its strong correlation with tumor growth, metastasis, poor survival, and drug resistance. Herein, we report the design, synthesis and structure-activity relationship (SAR) investigation of a series of pyrrolo[2,3-d]pyrimidine derivatives as new Axl inhibitors. Among them, the most promising compound 13b showed high enzymatic and cellular Axl potencies. Furthermore, 13b possessed preferable pharmacokinetic properties and displayed promising therapeutic effect in BaF3/TEL-Axl xenograft tumor model. Compound 13b may serve as a lead compound for new antitumor drug discovery.

PYRIDONE COMPOUNDS AND METHODS OF USE IN THE MODULATION OF A PROTEIN KINASE

The present disclosure relates generally to compounds and pharmaceutical compositions suitable as modulators of protein kinases, and methods for their use in treating disorders mediated, at least in part by, protein kinases.

MACROCYCLIC FUSED PYRRAZOLES AS MCL-1 INHIBITORS

Provided are compounds represented by Formula IA: (IA), and the pharmaceutically acceptable salts and solvates thereof, wherein R, R 1a, R 1b, L 1, L 2, L 3, X, A, B and C are as defined as set forth

Novel quinoline derivative inhibitor

The invention provides a novel quinoline derivative inhibitor, which has a structure represented by the following general formula (I). According to the invention, the compound provided by the invention can selectively inhibit tyrosine kinase TAM family/an

Synthesis of aryl β-ketoesters by opening of aryl epoxides with ethyl diazoacetate catalyzed by BF3OEt2

A facile synthesis of 4-aryl substituted β-ketoesters from the reaction aryl epoxides with ethyl diazoacetate, in presence of BF 3OEt2 has been described with excellent yields.

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.

PYRIDONE AMIDES AND ANALOGS EXHIBITING ANTI-CANCER AND ANTI-PROLIFERATIVE ACTIVITIES

Compounds useful in the treatment of mammalian cancers and especially human cancers according to Formula I are disclosed. Formula (I). Pharmaceutical compositions and methods of treatment employing the compounds disclosed herein are also disclosed.

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.

PYRIDONE AMIDES AND ANALOGS EXHIBITING ANTI-CANCER AND ANTI-PROLIFERATIVE ACTIVITES

Compounds useful in the treatment of mammalian cancers and especially human cancers according to Formula I are disclosed. Pharmaceutical compositions and methods of treatment employing the compounds disclosed herein are also disclosed.