2065-28-3

Usage

Uses

Used in Pharmaceutical Industry:
METHYL 5-METHYL-3-PHENYL-4-ISOXAZOLECARBOXYLATE is used as a key intermediate in the synthesis of various pharmaceuticals for its potential to contribute to the development of new drugs with diverse therapeutic applications.
Used in Agrochemical Industry:
In the agrochemical sector, METHYL 5-METHYL-3-PHENYL-4-ISOXAZOLECARBOXYLATE is employed as a building block in the creation of agrochemicals, leveraging its chemical properties to enhance crop protection and management.
Used in Chemical Research and Development:
METHYL 5-METHYL-3-PHENYL-4-ISOXAZOLECARBOXYLATE serves as a valuable tool in chemical research and development, where its unique structure is explored for potential applications in creating novel compounds with specific properties for various industries.

InChI:InChI=1/C12H11NO3/c1-8-10(12(14)15-2)11(13-16-8)9-6-4-3-5-7-9/h3-7H,1-2H3

Upstream product

• 67-56-1 methanol 
• 16883-16-2 5-methyl-3-phenylisoxazole-4-carbonyl chloride 
• 18913-35-4 methyl buta-2,3-dienoate 
• 698-16-8 benzohydroximoyl chloride 
• 109-99-9 tetrahydrofuran 
• 1136-45-4 5-methyl-3-phenylisoxazol-4-carboxylic acid 
• 105-45-3 acetoacetic acid methyl ester 
• 81745-44-0 benzohydroximoyl chloride 
• 873-67-6 benzonitrile oxide 
• 60753-84-6 α-chloro methyl crotonate 
• 100-52-7 benzaldehyde 
• 73967-70-1 methyl 3-(isopropylamino)but-2-enoate 
• 6249-80-5 1-phenylbut-3-en-1-one 
• 80735-94-0 1-Phenyl-3-buten-1-ol 

Downstream Products

• 95192-69-1 4-amino-4-phenyl-3-(methoxycarbonyl)-3-buten-2-one 
• 18718-79-1 5-methyl-3-phenyl-4-isoxazolylmethanol 
• 682352-79-0 5-bromomethyl-3-phenyl-isoxazole-4-carboxylic acid methyl ester 
• 682352-68-7 5-dibromomethyl-3-phenyl-isoxazole-4-carboxylic acid methyl ester 
• 682352-72-3 5-hydroxymethyl-3-phenyl-isoxazole-4-carboxylic acid methyl ester 
• 161126-45-0 5-formyl-3-phenyl-isoxazole-4-carboxylic acid methyl ester 
• 682352-97-2 5-(benzylamino-methyl)-3-phenyl-isoxazole-4-carboxylic acid 
• 682352-88-1 5-(benzylamino-methyl)-3-phenyl-isoxazole-4-carboxylic acid methyl ester 
• 87967-95-1 5-methyl-3-phenylisoxazole-4-carboxaldehyde 
• 635680-13-6 2-[hydroxy-(5-methyl-3-phenyl-isoxazol-4-yl)-methyl]-acrylic acid methyl ester 
• 1136-45-4 5-methyl-3-phenylisoxazol-4-carboxylic acid 
• 1391026-01-9 prop-2-ynyl 5-methyl-3-phenylisoxazole-4-carboxylate 
• 1391026-04-2 (1-(2-morpholino-2-oxoethyl)-1H-1,2,3-triazol-4-yl)methyl 5-methyl-3-phenylisoxazole-4-carboxylate 
• 1391026-05-3 (1-benzyl-1H-1,2,3-triazol-4-yl)methyl 5-methyl-3-phenylisoxazole-4-carboxylate 

Relevant academic research and scientific papers

Design and Structural Optimization of Dual FXR/PPARδActivators

Nonalcoholic steatohepatitis (NASH) is considered as severe hepatic manifestation of the metabolic syndrome and has alarming global prevalence. The ligand-activated transcription factors farnesoid X receptor (FXR) and peroxisome proliferator-activated receptor (PPAR) δhave been validated as molecular targets to counter NASH. To achieve robust therapeutic efficacy in this multifactorial pathology, combined peripheral PPAR?-mediated activity and hepatic effects of FXR activation appear as a promising multitarget approach. We have designed a minimal dual FXR/PPARδactivator scaffold by rational fusion of pharmacophores derived from selective agonists. Our dual agonist lead compound exhibited weak agonism on FXR and PPARδand was structurally refined to a potent and balanced FXR/PPARδactivator in a computer-aided fashion. The resulting dual FXR/PPARδmodulator comprises high selectivity over related nuclear receptors and activates the two target transcription factors in native cellular settings.

Catalyst- and solvent-free mechanochemical synthesis of isoxazoles from N-hydroxybenzimidoyl chlorides and enamino carbonyl compounds

A regioselective, solvent-free and catalyst-free synthesis of isoxazoles has been successfully developed under ball milling conditions. Milling the mixtures of N-hydroxybenzimidoyl chlorides and enamino carbonyl compounds in a ball mill at a frequency of

Design, Synthesis, and Biological Evaluation of Novel Nonsteroidal Farnesoid X Receptor (FXR) Antagonists: Molecular Basis of FXR Antagonism

Farnesoid X receptor (FXR) plays an important role in the regulation of cholesterol, lipid, and glucose metabolism. Recently, several studies on the molecular basis of FXR antagonism have been reported. However, none of these studies employs an FXR antagonist with nonsteroidal scaffold. On the basis of our previously reported FXR antagonist with a trisubstituted isoxazole scaffold, a novel nonsteroidal FXR ligand was designed and used as a lead for structural modification. In total, 39 new trisubstituted isoxazole derivatives were designed and synthesized, which led to pharmacological profiles ranging from agonist to antagonist toward FXR. Notably, compound 5s (4′-[(3-{[3-(2-chlorophenyl)-5-(2-thienyl)isoxazol-4-yl]methoxy}-1H-pyrazol-1-yl)methyl]biphenyl-2-carboxylic acid), containing a thienyl-substituted isoxazole ring, displayed the best antagonistic activity against FXR with good cellular potency (IC50=12.2±0.2μM). Eventually, this compound was used as a probe in a molecular dynamics simulation assay. Our results allowed us to propose an essential molecular basis for FXR antagonism, which is consistent with a previously reported antagonistic mechanism; furthermore, E467 on H12 was found to be a hot-spot residue and may be important for the future design of nonsteroidal antagonists of FXR. X marks the spot: 39 trisubstituted isoxazoles were designed and synthesized, leading to compounds with pharmacological profiles ranging from agonist to antagonist at the farnesoid X receptor (FXR). By using the most potent antagonist as a probe, the essential molecular basis of FXR antagonism is proposed, and E467 on H12 can be regarded as a hot-spot residue for the future design of nonsteroidal antagonists of FXR.

Oxime-mediated facile access to 5-methylisoxazoles and applications in the synthesis of valdecoxib and oxacillin

A palladium-catalyzed efficient synthesis of 5-methylisoxazoles via oxime-mediated functionalization of unactivated olefins is described. The reaction affords a variety of 5-methylisoxazoles in moderate to good yields. To further demonstrate the utility of the method, the rapid synthesis of valdecoxib and oxacillin is reported. (Chemical Equation Presented).

Synthesis of 1,2,3-triazole substituted isoxazoles via copper (I) catalyzed cycloaddition

The synthesis of a series of 3,5-disubstituted isoxazole-4-carboxylic esters containing N-substituted 1,2,3-triazoles (V) starting from various benzaldehydes (I) is reported. Benzaldehydes undergo oximation with hydroxylamine hydrosulfate. Later, chlorination followed by condensation with methylacetoacetate and the hydrolysis of the resulting ester afforded respective carboxylic acid (II), which on chlorination with PCl5 gave the corresponding acid chlorides (III). The coraboxylic acid chlorides (III) on propargylation gave propargylic esters (IV) and these on click reaction gave the title compounds (V).

Efficient regioselective synthesis of 4- and 5-substituted isoxazoles under thermal and microwave conditions

(Chemical Equation Presented) The [2+3] cycloaddition reaction between nitrile oxides 2 and the captodative olefins 1 or the methyl crotonate derivatives 4 is regioselective and leads to the formation of the 5-substituted amino-isoxazole 3 or the 4-substi

Inhibitors of c-Jun N terminal kinases (JNK) and other protein kinases

The present invention provides compounds of formula I: 1where R1 is H, CONH2, T(n)—R, or T(n)—Ar2, n may be zero or one, and G, XYZ, and Q are as described below. These compounds are inhibitors of protein kinase, particularly inhibitors of JNK, a mammalian protein kinase involved cell proliferation, cell death and response to extracellular stimuli. The invention also relates to methods for producing these inhibitors. The invention also provides pharmaceutical compositions comprising the inhibitors of the invention and methods of utilizing those compositions in the treatment and prevention of various disorders.