103344-70-3

Basic information

• Product Name: 2-hydroxy-4-oxo-4-phenylbut-2-enoic acid
• Synonyms: 2-hydroxy-4-oxo-4-phenylbut-2-enoic acid
• CAS NO: 103344-70-3
• Molecular Formula: C₁₀H₈O₄
• Molecular Weight: 192.16812
• Mol File: 103344-70-3.mol

Chemical Properties

• Melting Point: 149-150 °C (decomp)(Solv: water (7732-18-5); ethanol (64-17-5))
• Boiling Point: 371.4±42.0 °C(Predicted)
• Appearance: /
• Density: 1.377±0.06 g/cm3(Predicted)
• PKA: 3.33±0.19(Predicted)
• CAS DataBase Reference: 2-hydroxy-4-oxo-4-phenylbut-2-enoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 2-hydroxy-4-oxo-4-phenylbut-2-enoic acid(103344-70-3)
• EPA Substance Registry System: 2-hydroxy-4-oxo-4-phenylbut-2-enoic acid(103344-70-3)

Safety Data

• Hazardous Substances Data: 103344-70-3(Hazardous Substances Data)

Upstream product

• 55991-67-8 5-phenylfuran-2,3-dione 
• 88330-79-4 ethyl-(Z)-2-hydroxy-4-oxo-4-phenyl-but-2-enoate 
• 1232682-46-0 C₁₃H₁₂O₄ 
• 71-43-2 benzene 
• 98-86-2 acetophenone 
• 95-92-1 oxalic acid diethyl ester 
• 39847-99-9 (Z)-methyl 2-hydroxy-4-oxo-4-phenylbut-2-enoate 

Downstream Products

• 55558-80-0 2-hydroxy-6-phenylpyrimidine-4-carboxylic acid 
• 1327963-59-6 2-hydroxy-N-(3-metoxyphenyl)-6-phenylpyrimidine-4-carboxamide 
• 1328915-36-1 N-allyl-2-hydroxy-6-phenylpyrimidine-4-carboxamide 
• 1378840-87-9 C₁₀H₁₂O₄ 
• 1198396-82-5 2-((3-(Ethoxycarbonyl)-4,5,6,7-tetrahydrobenzo[b]thiophen-2-yl)amino)-4-oxo-4-phenylbut-2-enoic acid 
• 406946-75-6 3-phenacylidene-3,4-dihydro-1H-pyrido<2,3-b>pyrazin-2-one 

Relevant articles and documents

Divergent synthesis of (quinoxalin-2-yl)-1,3-oxazines and pyrimido[1,6-a]quinoxalines via the cycloaddition reaction of acyl(quinoxalinyl)ketenes

A facile synthetic approach towards two distinct quinoxaline-based heterocyclic scaffolds has been developed from the cycloaddition of acyl(quinoxalinyl)ketenes with carbodiimides. The described reaction represents the first example of a divergent synthesis based on acyl(quinoxalinyl)ketenes providing (quinoxalin-2-yl)-1,3-oxazines or pyrimido[1,6-a]quinoxalines depending on the type of the acyl substituent in the ketenes. The key reactants, acyl(quinoxalinyl)ketenes, are generated in situ via the thermal decarbonylation of readily available pyrroloquinoxaline oxo-derivatives. The proposed diversity-oriented synthesis provides facile access to a library of skeletally diverse pharmaceutically interesting quinoxaline-based heterocycles from inexpensive reagents.

One-Pot Synthesis of Thieno[3,2- e]pyrrolo[1,2- a]pyrimidine Derivative Scaffold: A Valuable Source of PARP-1 Inhibitors

A new, efficient, and versatile one-pot cascade reaction of diverse Gewald's aminothiophenes, 2-hydroxy-4-oxobut-2-enoic acid, and derivatives of cyanoacetic acid catalyzed by Et3N is presented. It enables direct synthesis of diverse 1-(2-oxoethylidene)-2-oxothieno[3,2-e]pyrrolo[1,2-a]pyrimidine in good to excellent yields. The reaction exhibits a broad substrate scope and also presents an opportunity for further modification of the structure. The method offers a convenient practical alternative to the known procedures. The synthesized thieno[3,2-e]pyrrolo[1,2-a]pyrimidine scaffold is an important structural motif of new poly(ADP-ribose) polymerase (PARP) inhibitors, playing a useful role in multiple pharmacological applications.

Design, synthesis and biological evaluation of novel aryldiketo acids with enhanced antibacterial activity against multidrug resistant bacterial strains

Antimicrobial resistance (AMR) is a major health problem worldwide, because of ability of bacteria, fungi and viruses to evade known therapeutic agents used in treatment of infections. Aryldiketo acids (ADK) have shown antimicrobial activity against several resistant strains including Gram-positive Staphylococcus aureus bacteria. Our previous studies revealed that ADK analogues having bulky alkyl group in ortho position on a phenyl ring have up to ten times better activity than norfloxacin against the same strains. Rational modifications of analogues by introduction of hydrophobic substituents on the aromatic ring has led to more than tenfold increase in antibacterial activity against multidrug resistant Gram positive strains. To elucidate a potential mechanism of action for this potentially novel class of antimicrobials, several bacterial enzymes were identified as putative targets according to literature data and pharmacophoric similarity searches for potent ADK analogues. Among the seven bacterial targets chosen, the strongest favorable binding interactions were observed between most active analogue and S. aureus dehydrosqualene synthase and DNA gyrase. Furthermore, the docking results in combination with literature data suggest that these novel molecules could also target several other bacterial enzymes, including prenyl-transferases and methionine aminopeptidase. These results and our statistically significant 3D QSAR model could be used to guide the further design of more potent derivatives as well as in virtual screening for novel antibacterial agents.

Diketo acids and their amino acid/dipeptidic analogues as promising scaffolds for the development of bacterial methionine aminopeptidase inhibitors

Using diketoesters as the template, various derivatives were designed and the selected compounds were synthesized as bacterial methionine aminopeptidase (MetAP) inhibitors. The results of in vitro antibacterial screening revealed fifteen compounds (1a-c,

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The ligand (z)-2-(3-methoxyphenylamino)-4-oxo-4-phenylbut-2-enoic acid and its Ni (II) complex were synthesized and their antifungal activity against the fungi wood stain Mucor plumbeus was evaluated. The ligand displayed fungostatic activity while the Ni

Synthesis and AChE inhibiting activity of 2, 4 substituted 6-phenyl pyrimidines

Novel substituted pyrimidines were synthesized from methyl 2,4-dioxo-4-phenyl-butanoate (I-A) and urea, followed by Mitsunobu coupling of I-A with benzyl or allyl alcohol to give the corresponding 2-hydroxypyrimidine ethers in good yields. Saponification

A new chemo-enzymatic route to chiral 2-hydroxy-4-phenylbutyrates by combining lactonase-mediated resolution with hydrogenation over Pd/C

A new chemo-enzymatic route to both isomers of 2-hydroxy-4-phenylbutyric acid is reported. The key step is the lactonase-catalyzed hydrolysis of cis- and trans-2-hydroxy-4-phenyl-4-butyrolactones followed by hydrogenation over Pd/C to afford optically pure 2-hydroxy-4-phenylbutyric acid.

(Z)-2,2-Dimethyl-5-carboxymethylene-1,3-dioxolan-4-one: a new synthon for the synthesis of α,γ-diketoacid derivatives

The synthesis and reactivity of (Z)-2,2-dimethyl-5-carboxymethylene-1,3-dioxolan-4-one, a new and versatile synthon useful for the synthesis of selectively protected α,γ-diketoacid derivatives, are described. This new, protected form of hydroxyl fumaric a

INHIBITORS OF MYCOBACTERIUM TUBERCULOSIS MALATE SYNTHASE, METHODS OF MARKING AND USES THEREOF

The present invention provides aryl- or heteroaryl- diketo acid compounds effective to inhibit an activity of a Mycobacterial malate synthase enzyme or to inhibit a malate synthase activity in other bacteria having the enzyme. The compounds may be phenyl-

Facile synthesis of enantiopure 4-substituted 2-hydroxy-4butyrolactones using a robust Fusarium lactonase

A facile chemo-enzymatic process has been developed for producing stereoisomers of 4substituted 2-hydroxy-4-butyrolactones with good to excellent enantioselectivity. This process involves an easy separation of the diastereoisomers by column chromatography