16883-16-2

Usage

Uses

Used as Intermediate of oxacillin sodium.

Flammability and Explosibility

Notclassified

Synthesis

Benzaldehyde and hydroxylamine hydrochloride are oximeated under alkaline conditions to generate benzoxime, which is then chlorinated with chlorine to give benzoxime chloride. It is combined with ethyl acetoacetate to hydrolyze and chlorinated to obtain 5-Methyl-3-phenylisoxazole-4-carbonyl chloride.

InChI:InChI=1/C11H8ClNO2/c1-7-9(11(12)14)10(13-15-7)8-5-3-2-4-6-8/h2-6H,1H3

Upstream product

• 6249-80-5 1-phenylbut-3-en-1-one 
• 80735-94-0 1-Phenyl-3-buten-1-ol 
• 31295-65-5 4-bromo-5-methyl-3-phenylisoxazole 
• 1008-74-8 5-methyl-3-phenylisoxazole 
• 68843-67-4 1-phenyl-but-3-en-1-one oxime 
• 932-90-1 Benzaldoxime 
• 698-16-8 benzohydroximoyl chloride 
• 100-52-7 benzaldehyde 
• 2065-28-3 methyl 5-methyl-3-phenylisoxazole-4-carboxylate 
• 35166-26-8 5-methyl-3-phenyl-4-isoxazoloyl carboxylic acid 
• 1136-45-4 5-methyl-3-phenylisoxazol-4-carboxylic acid 

Downstream Products

• 62235-34-1 3-methyl-1-(5-methyl-3-phenyl-isoxazole-4-carbonyl)-6-nitro-1H-indazole 
• 66-79-5 oxacillin 
• 2065-28-3 methyl 5-methyl-3-phenylisoxazole-4-carboxylate 
• 61728-31-2 5-methyl-3-phenyl-isoxazole-4-carboxylic acid 2,2,2-trifluoro-ethyl ester 
• 24477-32-5 5-methyl-3-phenyl-isoxazole-4-carboxylic acid 4-sulfamoyl-phenethylamide 
• 53646-02-9 5-methyl-3-phenyl-isoxazole-4-carboxylic acid 2-nitro-anilide 
• 68055-50-5 1,2-Bis(3'-phenyl-5'-methyl-4'-isoxazolyl)hydrazine 
• 18336-75-9 5-methyl-3-phenylisoxazole-4-carbohydrazide 
• 106833-69-6 1-[(5-methyl-3-phenyl-4-isoxazolyl)carbonyl]-pyrrolidine 
• 55153-42-9 4-[(5-methyl-3-phenyl-4-isoxazolyl)carbonyl]-morpholine 
• 90515-57-4 5-Methyl-3-phenyl-isoxazole-4-carboxylic acid (4-hydroxy-2-oxo-2H-chromen-3-yl)-amide 
• 110984-58-2 (5-Amino-3-morpholin-4-yl-[1,2,4]triazol-1-yl)-(5-methyl-3-phenyl-isoxazol-4-yl)-methanone 
• 90515-60-9 5-Methyl-3-phenyl-isoxazole-4-carboxylic acid (6-chloro-4-hydroxy-2-oxo-2H-chromen-3-yl)-amide 
• 124953-38-4 1-[(5-methyl-3-phenyl-4-isoxazolyl)carbonyl]-piperazine 

Relevant academic research and scientific papers

Design, synthesis, and bioevaluation of substituted phenyl isoxazole analogues as herbicide safeners

Herbicide safeners enhance herbicide detoxification in crops without affecting target weed sensitivity. To enhance crop tolerance to the toxicity-related stress caused by the herbicide acetochlor (ACT), a new class of substituted phenyl isoxazole derivatives was designed by an intermediate derivatization method as herbicide safeners. Microwave-assisted synthesis was used to prepare the phenyl isoxazole analogues, and all of the structures were confirmed via IR, 1H NMR, 13C NMR, and HRMS. Compound I-1 was further characterized by X-ray diffraction analysis. Bioassay results showed that most of the obtained compounds provided varying degrees of safening against ACT-induced injury by increasing the corn growth recovery, glutathione content, and glutathione S-transferase activity. In particular, compound I-20 showed excellent safener activity against ACT toxicity, comparable to that of the commercial safener benoxacor. Gaussian calculations have been performed and the results indicated that the nucleophilic ability of compound I-20 is higher than that of benoxacor, thus the activity is higher than that of benoxacor. These findings demonstrate that phenyl isoxazole derivatives possess great potential for protective management in cornfields.

Synthesis, Identification, and Structure-Activity Relationship Analysis of GATA4 and NKX2-5 Protein-Protein Interaction Modulators

Transcription factors GATA4 and NKX2-5 directly interact and synergistically activate several cardiac genes and stretch-induced cardiomyocyte hypertrophy. Previously, we identified phenylisoxazole carboxamide 1 as a hit compound, which inhibited the GATA4-NKX2-5 transcriptional synergy. Here, the chemical space around the molecular structure of 1 was explored by synthesizing and characterizing 220 derivatives and structurally related compounds. In addition to the synergistic transcriptional activation, selected compounds were evaluated for their effects on transcriptional activities of GATA4 and NKX2-5 individually as well as potential cytotoxicity. The structure-activity relationship (SAR) analysis revealed that the aromatic isoxazole substituent in the southern part regulates the inhibition of GATA4-NKX2-5 transcriptional synergy. Moreover, inhibition of GATA4 transcriptional activity correlated with the reduced cell viability. In summary, comprehensive SAR analysis accompanied by data analysis successfully identified potent and selective inhibitors of GATA4-NKX2-5 transcriptional synergy and revealed structural features important for it.

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).

METHANETHIONE COMPOUNDS HAVING ANTIVIRAL ACTIVITY

A compound of formula (I), The compound is useful as an antiviral agent, in particular for the treatment of influenza. A method for preparing the compound of formula (I) and a composition comprising the compound of formula (I).

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).

Enantioselective halocyclization using reagents tailored for chiral anion phase-transfer catalysis

A chiral anion phase-transfer system for enantioselective halogenation is described. Highly insoluble, ionic reagents were developed as electrophilic bromine and iodine sources, and application of this system to o-anilidostyrenes afforded halogenated 4H-3,1-benzoxazines with excellent yield and enantioselectivity.

SUBSTITUTED AZOLE AROMATIC HETEROCYCLES AS INHIBITORS OF 11BETA-HSD-1

Compounds of formula I and IV are described and have therapeutic utility, particularly in the treatment of diabetes, obesity and related conditions and disorder: wherein the variables A-B, R1, R2, m, and Q are described herein.

ARYL-ISOXAZOL-4-YL-IMIDAZO[1, 5-A]PYRIDINE DERIVATIVES

The present invention is concerned with aryl-isoxazol-4-yl-imidazo[1,5-a]pyridine derivatives of formula (I) wherein: R1 is hydrogen, halogen, hydroxy, lower alkyl, benzyloxy or -O-(CH2)-(CO)-5 or 6 membered heteroaryl optionally substituted by aryl and lower alkyl; R2 is hydrogen, lower alkyl, or -(CO)-Ra; R3 is hydrogen, halogen, cyano, lower alkyl, or -(CO)-Ra; Ra is hydroxy, lower alkoxy, NR'R'', wherein R' and R'' are each independently hydrogen, cycloalkyl, 5 or 6-membered heterocycloalkyl or lower alkyl optionally substituted by cycloalkyl, cyano, 5 or 6-membered heterocycloalkyl or 5 or 6-membered heteroaryl; as well as pharmaceutically acceptable acid addition salts thereof. It has been found that this class of compounds show high affinity and selectivity for GABA A α5 receptor binding sites and might be useful as cognitive enhancer or for the treatment of cognitive disorders like Alzheimer's disease.

Identification of a series of highly potent activators of the Nurr1 signaling pathway

The nuclear receptor Nurr1 (NR4A2) is critically involved in the development and maintenance of midbrain dopaminergic neurons and is believed to function independently of endogenous activation. The hit identification and SAR studies leading to isoxazolo-pyridinone 7e, a highly potent, brain penetrable activator of the Nurr1 signaling pathway, are described.

Straightforward transformation of isoxazoles into pyrazoles: renewed and improved

Isoxazoles bearing alkyl or carbamoyl groups were transformed into the corresponding pyrazoles in high yields by the treatment with hydrazine in methanol in the presence of a hydrogenation catalyst, e.g., Raney nickel, at ambient temperature. For the synthesis of N-substituted pyrazoles, hydrogenolysis of isoxazole followed by the treatment with substituted hydrazine was required. 3(5)-Aryl- or acylamido-substituted isoxazoles are less suitable for such transformations.