5817-92-5

Usage

Uses

Used in Pharmaceutical and Agrochemical Industries:
2,4-dioxo-4-phenylbutanoic acid is used as an intermediate in the synthesis of various pharmaceuticals and agrochemicals due to its versatile chemical structure, which can be further modified to produce a range of active compounds.
Used in Fragrance and Flavoring Agent Production:
It serves as a key intermediate in the production of fragrances and flavoring agents, capitalizing on its ability to contribute to the creation of aromatic and taste profiles in consumer products.
Used in the Synthesis of Amphetamines:
2,4-dioxo-4-phenylbutanoic acid is also a crucial component in the synthesis of amphetamines, highlighting its importance in the chemical synthesis of certain psychoactive substances.
Used in Research and Development:
2,4-dioxo-4-phenylbutanoic acid is utilized in research settings to explore its antimicrobial and anti-inflammatory properties, potentially leading to the development of new therapeutic agents.
It is important to handle 2,4-dioxo-4-phenylbutanoic acid with care due to its irritant properties to the skin, eyes, and respiratory system, ensuring safety in its application across various industries.

Upstream product

• 6296-54-4 ethyl 2,4-dioxo-4-phenylbutyrate 
• 41158-32-1 methyl 4-oxo-4-phenylbut-2-ynoate 
• 20577-73-5 methyl 4-phenyl-2,4-dioxobutanoate 
• 93-58-3 benzoic acid methyl ester 
• 129661-87-6 pyruvic acid N,N-dimethylhydrazone 
• 124-38-9 carbon dioxide 
• 7647-01-0 hydrogenchloride 
• 66286-48-4 2,4-dioxo-4-phenyl-butyric acid amide 
• 98-86-2 acetophenone 
• 141-78-6 ethyl acetate 
• 120-46-7 1,3-diphenylpropanedione 
• 95-92-1 oxalic acid diethyl ester 
• 41167-58-2 2-hydroxy-4-oxo-4-phenyl-but-2-enoic acid methyl ester 
• 88330-82-9 ethyl benzoylpyruvate, sodium salt 

Downstream Products

• 13983-60-3 2-hydroxy-4-phenyl-4-butyrolactone 
• 5071-61-4 5-phenyl-1H-pyrazole-3-carboxylic acid 
• 4437-14-3 (E)-5,5'-diphenyl-3,3'-bifuranylidene-2,2'-dione 
• 112273-10-6 2-phenyl-naphth[2',3':4,5]imidazo[1,2-a]pyrimidine 
• 110554-31-9 2,4-dioxo-1,7-diphenyl-1,2,3,4-tetrahydro-pyrido[2,3-d]pyrimidine-5-carboxylic acid 
• 860560-23-2 2-benzoyl-3-phenyl-benzo[f]quinoline-1-carboxylic acid 
• 175350-44-4 4-benzoyl-1,5-diphenyl-pyrrolidine-2,3-dione 
• 65387-40-8 α-phenylaminobenzoylacrylic acid 
• 22298-77-7 3-phenacylidene-3,4-dihydro-1H-quinoxalin-2-one 
• 22298-79-9 3-(2-oxo-2-phenyl-ethyl)-1-phenyl-1H-quinoxalin-2-one 
• 64393-75-5 2-(2-oxo-2-phenyl-ethylidene)-4H-benzo[1,4]thiazin-3-one 
• 59079-03-7 (Z)-2-Methoxy-4-oxo-4-phenyl-but-2-enoic acid methyl ester 
• 55991-67-8 5-phenylfuran-2,3-dione 
• 152034-68-9 2-(5-amino-3-methyl-1-phenyl-4-pyrazolylamino)-4-phenyl-4-oxo-2-butenoic acid 

Relevant academic research and scientific papers

Synthesis of Unnatural α-Amino Acid Derivatives via Light-Mediated Radical Decarboxylative Processes

Unnatural amino acids (UAAs) are key building blocks with widespread application across several scientific fields. Therefore, it is highly attractive to develop straightforward and simple methodologies capable of granting quick access to these species. Herein we report a light-mediated protocol for the synthesis of UAA via radical decarboxylative processes. This methodology, which employs readily available and abundant starting materials – such as carboxylic and α-keto acids – proceeds under very mild reaction conditions and shows a high functional group tolerance. In addition, the products of the radical reaction can be readily derivatized to grant rapid access to complex UAAs. (Figure presented.).

Non-peptide-based new class of platelet aggregation inhibitors: Design, synthesis, bioevaluation, SAR, and in silico studies

A series of 2-oxo-2-phenylethylidene linked 2-oxo-benzo[1,4]oxazine analogues 17a–x and 18a–o, incorporated with a variety of electron-withdrawing as well as electron-donating groups at ring A and ring C, were synthesized under greener conditions in excel

Furan-2,3-diones as masked dipoles: synthesis of isotetronic acids and mechanistic considerations

The formal dipolar behaviour of furan-2,3-diones is illustrated by their reaction with ethyl glyoxylate under Lewis basic activation uniquely, giving access to isotetronic derivatives. The Janus-type nature of the activated species, both nucleophilic and

Targeting inactive enzyme conformation: Aryl diketoacid derivatives as a new class of PTP1B inhibitors

There has been considerable interest in protein tyrosine phosphatase 1B (PTP1B) as a therapeutic target for diabetes, obesity, as well as cancer. Identifying inhibitory compounds with good bioavailability is a major challenge of drug discovery programs targeted toward PTPs. Most current PTP active site-directed pharmacophores are negatively charged pTyr mimetics which cannot readily enter the cell. This lack of cell permeability limits the utility of such compounds in signaling studies and further therapeutic development. We identify aryl diketoacids as novel pTyr surrogates and show that neutral amide-linked aryl diketoacid dimers also exhibit excellent PTP inhibitory activity. Kinetic studies establish that these aryl diketoacid derivatives act as noncompetitive inhibitors of PTP1B. Crystal structures of ligand-bound PTP1B reveal that both the aryl diketoacid and its dimeric derivative bind PTP1B at the active site, albeit with distinct modes of interaction, in the catalytically inactive, WPD loop open conformation. Furthermore, dimeric aryl diketoacids are cell permeable and enhance insulin signaling in hepatoma cells, suggesting that targeting the inactive conformation may provide a unique opportunity for creating active site-directed PTP1B inhibitors with improved pharmacological properties.

Enantio- and regiospecific reduction of ethyl 4-phenyl-2,4-dioxobutyrate with baker's yeast: Preparation of (R)-HPB ester

Ethyl 2,4-dioxo-4-phenylbutyrate obtained by condensation of acetophenone with diethyl oxalate is reduced enantio- and regiospecifically by baker's yeast in a diisopropyl ether/water two-phase system to give (-)-ethyl (R)-2-hydroxy-4-oxo-4-phenylbutyrate with an ee = 98% in 80% isolated yield. The hydroxyester was hydrogenated over Pd-C to obtain (-)-ethyl (R)-2-hydroxy-4-phenylbutyrate (HPB ester), an important intermediate for the synthesis of ACE inhibitors. Prolonged contact of the reduction product with baker's yeast produced 3-phenyl 3-oxo propanol in 90% yield.

Slow-binding inhibition of 2-keto-3-deoxy-6-phosphogluconate (KDPG) aldolase

2-Keto-3-deoxy-6-phosphogluconate (KDPG) aldolase is a key enzyme in the Entner-Doudoroff pathway of bacteria. It catalyzes the reversible production of KDPG from pyruvate and D-glyceraldehyde 3-phosphate through a class I Schiff base mechanism. On the basis of aldolase mechanistic pathway, various pyruvate analogues bearing β-diketo structures were designed and synthesized as potential inhibitors. Their capacity to inhibit aldolase catalyzed reaction by forming stabilized iminium ion or conjugated enamine were investigated by enzymatic kinetics and UV-vis difference spectroscopy. Depending of the substituent R (methyl or aromatic ring), a competitive or a slow-binding inhibition takes place. These results were examined on the basis of the three-dimensional structure of the enzyme.

Discovery of α,γ-Diketo Acids as Potent Selective and Reversible Inhibitors of Hepatitis C Virus NS5b RNA-Dependent RNA Polymerase

α,γ-Diketo acids (DKA) were discovered from screening as selective and reversible inhibitors of hepatitis C virus NS5b RNA-dependent RNA polymerase. The diketo acid moiety proved essential for activity, while substitution on the γ position was necessary for selectivity and potency. Optimization led to the identification of a DKA inhibitor of NS5b polymerase with IC50 = 45 nM, one of the most potent HCV NS5b polymerase inhibitors reported.

The identification and optimization of 2,4-diketobutyric acids as flap endonuclease 1 inhibitors

Flap endonuclease 1 (FEN1) is a key enzyme involved in base excision repair (BER), a primary pathway utilized by mammalian cells to repair DNA damage. In this report, we describe the identification and SAR of a series of 2,4-diketobutyric acid FEN1 inhibi

Pyruvic Acid Dimethylhydrazone. A Synthetic Equivalent of the Pyruvic Acid Dianion

The pyruvic acid dimethyl hydrazone can be easily prepared in ether.This compound, after deprotonation with alkyllithium, forms a strong nucleophile which on tratment with electrophiles and acidic work up yield α-ketoacids, α-hydroxybutenolides or α,γ-diketoacids.