39847-99-9

Basic information

• Product Name: 2-Butenoic acid, 2-hydroxy-4-oxo-4-phenyl-, methyl ester, (2Z)-
• CAS NO: 39847-99-9
• Molecular Formula: C11H10O4
• Molecular Weight: 206.198
• Mol File: 39847-99-9.mol

Chemical Properties

• CAS DataBase Reference: 2-Butenoic acid, 2-hydroxy-4-oxo-4-phenyl-, methyl ester, (2Z)-(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Butenoic acid, 2-hydroxy-4-oxo-4-phenyl-, methyl ester, (2Z)-(39847-99-9)
• EPA Substance Registry System: 2-Butenoic acid, 2-hydroxy-4-oxo-4-phenyl-, methyl ester, (2Z)-(39847-99-9)

Safety Data

• Hazardous Substances Data: 39847-99-9(Hazardous Substances Data)

Upstream product

• 125179-77-3 methyl 4-oxo-4-phenyl-2-p-bromophenylamino-Z-2-butenoate 
• 67-56-1 methanol 
• 98-86-2 acetophenone 
• 95-92-1 oxalic acid diethyl ester 
• 553-90-2 Dimethyl oxalate 
• 113416-21-0 methyl ester of 4-phenyl-2-phenylamino-4-oxo-2-butenoic acid 
• 55991-67-8 5-phenylfuran-2,3-dione 

Downstream Products

• 126324-65-0 methyl ester of 4-phenyl-2-(p-tolylamino)-4-oxo-2-butenoic acid 
• 235789-28-3 methyl 5-phenyl-1-(2-pyridyl)pyrazole-3-carboxylate 
• 309922-52-9 4-benzoyl-1-(2-dimethylamino-ethyl)-3-hydroxy-5-(4-methoxy-phenyl)-1,5-dihydro-pyrrol-2-one 
• 337923-14-5 4-benzoyl-1-(2-dimethylamino-ethyl)-3-hydroxy-5-(2-methoxy-phenyl)-1,5-dihydro-pyrrol-2-one 
• 32781-14-9 (Z)-6-chloro-3-(2-oxo-2-phenylethylidene)-3,4-dihydro-2H-benzo[b][1,4]oxazin-2-one 
• 1046152-03-7 methyl 1-(4-methanesulfonylphenyl)-5-phenyl-1H-pyrazole-3-carboxylate 
• 887761-84-4 3-benzoyl-8-chloro-1,2-dihydro-4H-pyrrolo[2,1-c][1,4]benzoxazine-1,2,4-trione 

Relevant articles and documents

Synthesis of the ligand (z)-2-(3-methoxyphenylamino)-4-oxo-4-phenylbut-2- enoic acid and its antifungal activity against the wood stain fungi mucor plumbeus

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

Kinetics of opening of the ring of 5-aryl-2,3-dihydrofuran-2,3-diones under the influence of methanol

The kinetics of the opening of the ring of 5-aryl-2,3-dihydrofuran-2,3-diones under the influence of methanol, which leads to the formation of methyl esters of aroylpyruvic acids, were studied by PMR spectroscopy. A mechanism is proposed for the reaction.

Stereoselective Synthesis of Quaternary Pyrrolidine-2,3-diones and β-Amino Acids

A facile, diastereoselective synthesis of highly substituted pyrrolidine-2,3-diones is reported, along with the one-step conversion of these heterocycles to novel β-amino acids and further functionalized derivatives. This method involves an unusually mild, one-pot, three-component cyclization/allylation followed by a Claisen rearrangement to provide unusual pyrrolidinone products that are densely functionalized and contain an all-carbon quaternary stereocenter. The reported reaction sequence is operationally simple, exquisitely diastereoselective, and provides gram-scale access to valuable heterocyclic scaffolds and β-amino acids not readily accessible via existing approaches.

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

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-

Diazen-1-ium-1,2-diolated nitric oxide donor ester prodrugs of 1-(4-methanesulfonylphenyl)-5-aryl-1H-pyrazol-3-carboxylic acids: Synthesis, nitric oxide release studies and anti-inflammatory activities

A new group of hybrid nitric oxide-releasing anti-inflammatory drugs (NONO-coxibs) wherein an O2-acetoxymethyl-1-(N-ethyl-N-methylamino)diazen-1-ium-1,2-diolate (11a-c) NO-donor moiety is attached directly to the carboxylic acid group of 1-(4-methanesulfonylphenyl)-5-aryl-1H-pyrazol-3-carboxylic acids were synthesized. The diazen-1-ium-1,2-diolate compounds 11a-c all released a low amount of NO upon incubation with phosphate buffer (PBS) at pH 7.4 (7.7-9.3% range). In comparison, the percentage of NO released was significantly higher (67.5-73.6% of the theoretical maximal release of two molecules of NO/molecule of the parent hybrid ester prodrug) when the diazen-1-ium-1,2-diolate ester prodrugs were incubated in the presence of rat serum. These incubation studies suggest that both NO and the anti-inflammatory 1-(4-methanesulfonylphenyl)-5-(4-H, 4-F or 4-Me-phenyl)-1H-pyrazol-3-carboxylic acid (9a-c) would be released from the parent NONO-coxib upon in vivo cleavage by non-specific serum esterases. The 1-(4-methanesulfonylphenyl)-5-(4-H, 4-F or 4-Me-phenyl)-1H-pyrazol-3-carboxylic acids (9a-c) exhibited AI activities (ID50 = 85.2-104.4 mg/kg po range) between that exhibited by the reference drugs aspirin (ID50 = 128.7 mg/kg po) and celecoxib (ID50 = 10.8 mg/kg po). Hybrid ester anti-inflammatory/NO-donor prodrugs (NONO-coxibs) offers a potential drug design concept targeted toward the development of anti-inflammatory drugs that are devoid of adverse ulcerogenic and/or cardiovascular effects.

From ligand to complexes: Inhibition of human immunodeficiency virus type 1 integrase by β-diketo acid metal complexes

β-Diketo acid-containing compounds are a promising class of human immunodeficiency virus type 1 (HIV-1) integrase (IN) inhibitors. Starting from the hypothesis that these inhibitors are able to coordinate ions in solution before interacting on the active site, a series of potentiometric measurements have been performed to understand the coordination ability of the diketo acid pharmacophore toward the biologically relevant Mg2+. Moreover, by using β-diketo acid/ester as model ligands with a set of divalent metal ions (Mg, Mn, Ni, Co, Cu, and Zn), we obtained a series of complexes and tested them for anti-HIV-1 IN activity. Results demonstrate that the diketo acid functionality chelates divalent metal ions in solution, and complexes with metals in different stoichiometric ratios are isolated. We postulate that the diketo acids act as complexes in their active form. In particular, they predominantly form species such as Mg2L2+ and Mg 2L2 (derived from diketo acids, H2L), and MgL+ and MgL2 (derived from diketo esters, HL) at physiological pH. Furthermore, the synthesized mono- and dimetallic complexes inhibited IN at a high nanomolar to low micromolar range, with metal dependency in the phenyl diketo acid series. Retrospective analysis suggests that the electronic properties of the aromatic framework influence the metal-chelating ability of the diketo acid system. Therefore, the difference in activities is related to the complexes they preferentially form in solution, and these findings are important for the design of a new generation of IN inhibitors.

Improved preparation and structural investigation of 4-aryl-4-oxo-2- hydroxy-2-butenoic acids and methyl esters

A simple and efficient oxalylation of aryl methyl ketones was accomplished with dimethyl oxalate in the presence of sodium methoxide. The unpreviously reported sodium ketoenolate esters were isolated and gently hydrolyzed into the ketoenol esters in good yields. Alternatively the sodium ketoenolate esters hydrolysis could also be conducted to directly afford the ketoenol acids, which represent one of the most promising class of HIV-1 integrase inhibitors. Advantages over previously reported procedures were better yields and simplicity of the purification protocol.

Synthesis and SAR of 4-aryl-2-hydroxy-4-oxobut-2-enoic acids and esters and 2-amino-4-aryl-4-oxobut-2-enoic acids and esters: Potent inhibitors of kynurenine-3-hydroxylase as potential neuroprotective agents

The synthesis and structure-activity relationship of a series of 4-aryl- 2-hydroxy-4-oxobut-2-enoic acids and esters and 2-amino-4-aryl-4-oxobut-2- enoic acids and esters as potent inhibitors of kynurenine-3-hydroxylase are described. These compounds are

Study of the Mechanisms of Reactions of 1,3-Dicarbonyl Compounds with Nucleophilic Reagents: X. Kinetics of the Hydrolysis of Methyl 4-Aryl-2-Arylamino-4-Oxobut-2-Enoates

The kinetics of hydrolysis of methyl 4-aryl-2-arylamino-4-oxobut-2-enoates in 50% aqueous dioxane in the presence of acetate and monochloroacetate buffer solutions was studied by spectrophotometry. An analysis of the dependence of the rate of hydrolysis on the concentrations and the composition of the components of the solutions and on the nature of the substituents in the substrate made it possible to propose a mechanism of general acid catalysis of the reaction.