4357-94-2

Usage

Uses

Used in Pharmaceutical Industry:
METHYL 3-(2-CHLOROPHENYL)-5-METHYL-4-ISOXAZOLECARBOXYLATE is used as a building block for the synthesis of pharmaceuticals due to its potential biological activities, such as anti-inflammatory and analgesic properties. Its versatile nature allows it to be incorporated into various drug formulations for the treatment of different medical conditions.
Used in Agrochemical Industry:
METHYL 3-(2-CHLOROPHENYL)-5-METHYL-4-ISOXAZOLECARBOXYLATE is used as a building block in the development of agrochemicals, specifically for its insecticidal and acaricidal activities. It contributes to the creation of pesticide products that help control and manage pests in agricultural settings, thereby protecting crops and enhancing overall agricultural productivity.

InChI:InChI=1/C12H10ClNO3/c1-7-10(12(15)16-2)11(14-17-7)8-5-3-4-6-9(8)13/h3-6H,1-2H3

Upstream product

• 105-45-3 acetoacetic acid methyl ester 
• 29568-74-9 2-chloro-N-hydroxybenzimidoyl chloride 
• 89-98-5 2-chloro-benzaldehyde 
• 67-56-1 methanol 
• 25629-50-9 3-(2-chlorophenyl)-5-methylisoxazole-4-carbonyl chloride 
• 3717-28-0 2-chloro benzaldehyde oxime 

Downstream Products

• 23598-72-3 3-(2-chlorophenyl)-5-methyl-4-isoxazolecarboxylic acid 
• 682352-75-6 3-(2-chloro-phenyl)-5-hydroxymethyl-isoxazole-4-carboxylic acid methyl ester 
• 682352-82-5 5-bromomethyl-3-(2-chloro-phenyl)-isoxazole-4-carboxylic acid methyl ester 
• 682352-71-2 3-(2-chloro-phenyl)-5-dibromomethyl-isoxazole-4-carboxylic acid methyl ester 
• 388608-83-1 3-(2-chlorophenyl)-5-methylisoxazole-4-carboxaldehyde 
• 635680-61-4 2-{[3-(2-chlorophenyl)-5-methylisoxazol-4-yl]hydroxymethyl}acrylonitrile 
• 627882-17-1 2-{[3-(2-chlorophenyl)-5-methylisoxazol-4-yl]hydroxymethyl}acrylic acid methyl ester 
• 635681-06-0 acetic acid 1-[3-(2-chlorophenyl)-5-methylisoxazol-4-yl]-2-cyanoallyl ester 
• 627882-29-5 2-{acetoxy-[3-(2-chlorophenyl)-5-methylisoxazol-4-yl]methyl}acrylic acid methyl ester 
• 1059608-82-0 C₂₆H₂₃ClNO₅P 

Relevant academic research and scientific papers

PD(II)-Catalyzed ligand-controlled synthesis of 2,3-dihydroisoxazole-4-carboxylates and bis(2,3-dihydroisoxazol-4-Yl)methanones

Pd(II)-catalyzed ligand-controlled switching between cyclization-carbonylation and cyclization-carbonylation-cyclization-coupling(CCC-coupling) reactions of propargylic N-hydroxylamines was investigated. The use of a [Pd(tfa)2(box)] catalyst in MeOH affor

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.

PHENYL-ISOXAZOL DERIVATIVES AND PREPARATION PROCESS THEREOF

Disclosed are a phenyl-isoxazol derivative compound, which is useful as a treatment material for virus infection, especially, infection of an influenza virus, or its pharmaceutically acceptable derivative, a preparation method thereof, and an illness treatment pharmaceutical composition including the compound as an active ingredient.

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).

PHENYL-ISOXAZOL DERIVATIVES AND PREPARATION PROCESS THEREOF

Disclosed are a phenyl-isoxazol derivative compound, which is useful as a treatment material for virus infection, especially, infection of an influenza virus, or its pharmaceutically acceptable derivative, a preparation method thereof, and an illness treatment pharmaceutical composition including the compound as an active ingredient

β-Ketophosphonates as β-lactamase inhibitors: Intramolecular cooperativity between the hydrophobic subsites of a class D β-lactamase

A series of aryl and arylmethyl β-aryl-β-ketophosphonates have been prepared as potential β-lactamase inhibitors. These compounds, as fast, reversible, competitive inhibitors, were most effective (micromolar Ki values) against the class D OXA-1 β-lactamase but had less activity against the OXA-10 enzyme. They were also quite effective against the class C β-lactamase of Enterobacter cloacae P99 but less so against the class A TEM-2 enzyme. Reduction of the keto group to form the corresponding β-hydroxyphosphonates led to reduced inhibitory activity. Molecular modeling, based on the OXA-1 crystal structure, suggested interaction of the aryl groups with the hydrophobic elements of the enzyme's active site and polar interaction of the keto and phosphonate groups with the active site residues Ser 115, Lys 212 and Thr 213 and with the non-conserved Ser 258. Analysis of binding free energies showed that the β-aryl and phosphonate ester aryl groups interacted cooperatively within the OXA-1 active site. Overall, the results suggest that quite effective inhibitors of class C and some class D β-lactamases could be designed, based on the β-ketophosphonate platform.

Highly substituted isoxazoles: The Baylis-Hillman reaction of substituted 4-isoxazolecarbaldehydes and attempted cyclization to isoxazole-annulated derivatives

In an attempt to understand the effect of position of the formyl group on the efficiency of Baylis-Hillman reaction within isoxazolecarbaldehydes, the reactions of substituted 4-isoxazolecarbaldehydes to obtain highly substituted isoxazoles are described. Attempts to obtain isoxazole-annulated derivatives from these Baylis-Hillman adducts involving SNR′-SNAr substitution strategy are also described.