1136-45-4

Usage

Uses

Used in Pharmaceutical Industry:
5-Methyl-3-phenylisoxazole-4-carboxylic acid is used as an intermediate in the synthesis of various pharmaceutical compounds, particularly penicillins. Its role in the preparation of intermediates is crucial for the development of new antibiotics, which are essential for treating bacterial infections.
Used in Chemical Synthesis:
In the field of chemical synthesis, 5-Methyl-3-phenylisoxazole-4-carboxylic acid is utilized for acylation during the solid support synthesis of isoxazolopyridone derivatives. These derivatives have potential applications in various industries, including pharmaceuticals, agrochemicals, and materials science, due to their diverse chemical properties and potential biological activities.

InChI:InChI=1/C11H9NO3/c1-7-9(11(13)14)10(12-15-7)8-5-3-2-4-6-8/h2-6H,1H3,(H,13,14)

Upstream product

• 873-67-6 benzonitrile oxide 
• 590-93-2 2-Butynoic acid 
• 87967-95-1 5-methyl-3-phenylisoxazole-4-carboxaldehyde 
• 1143-82-4 ethyl 5-methyl-3-phenylisoxazole-4-carboxylate 
• 14205-42-6 3-dimethylamino-crotonic acid ethyl ester 
• 698-16-8 benzohydroximoyl chloride 
• 6497-25-2 4-ethenyl-5-methyl-3-phenyl-1,2-oxazole 
• 50401-64-4 3-phenyl-4-acetyl-5-isoxazolone 
• 100-52-7 benzaldehyde 
• 105-45-3 acetoacetic acid methyl ester 
• 31295-65-5 4-bromo-5-methyl-3-phenylisoxazole 
• 80735-94-0 1-Phenyl-3-buten-1-ol 
• 6249-80-5 1-phenylbut-3-en-1-one 
• 100-47-0 benzonitrile 

Downstream Products

• 1008-74-8 5-methyl-3-phenylisoxazole 
• 16883-16-2 5-methyl-3-phenylisoxazole-4-carbonyl chloride 
• 38694-05-2 5-methyl-3-(3-nitrophenyl)isoxazole-4-carboxylic acid 
• 106833-69-6 1-[(5-methyl-3-phenyl-4-isoxazolyl)carbonyl]-pyrrolidine 
• 55153-42-9 4-[(5-methyl-3-phenyl-4-isoxazolyl)carbonyl]-morpholine 
• 544681-96-1 N-[4-(diethylamino)phenyl]-5-methyl-3-phenylisoxazole-4-carboxamide 
• 123862-91-9 5-methyl-3-phenyl-4-(N-phenylcarbamoyl)isoxazole 
• 38694-07-4 3-(3-amino-phenyl)-5-methyl-isoxazole-4-carboxylic acid 
• 91842-83-0 1-Amino-1-(3-amino-phenyl)-buten-⁽¹⁾-on-⁽³⁾ 
• 92286-61-8 3-(3-hydroxy-phenyl)-5-methyl-isoxazole-4-carboxylic acid 
• 93002-09-6 3-(3-methoxy-phenyl)-5-methyl-isoxazole-4-carboxylic acid 
• 94541-73-8 3-(3-hydroxy-phenyl)-5-methyl-isoxazole-4-carboxylic acid anilide 
• 1736-18-1 3-(3-fluorophenyl)-5-methylisoxazol-4-carboxylic acid 
• 1960-92-5 methyl 3-(3-fluorophenyl)-5-methylisoxazole-4-carboxylate 

Relevant academic research and scientific papers

Stem cells are the most sensitive screening tool to identify toxicity of GATA4-targeted novel small-molecule compounds

Safety assessment of drug candidates in numerous in vitro and experimental animal models is expensive, time consuming and animal intensive. More thorough toxicity profiling already in the early drug discovery projects using human cell models, which more closely resemble the physiological cell types, would help to decrease drug development costs. In this study we aimed to compare different cardiac and stem cell models for in vitro toxicity testing and to elucidate structure–toxicity relationships of novel compounds targeting the cardiac transcription factor GATA4. By screening the effects of eight compounds at concentrations ranging from 10?nM up to 30?μM on the viability of eight different cell types, we identified significant cell type- and structure-dependent toxicity profiles. We further characterized two compounds in more detail using high-content analysis. The results highlight the importance of cell type selection for toxicity screening and indicate that stem cells represent the most sensitive screening model, which can detect toxicity that may otherwise remain unnoticed. Furthermore, our structure–toxicity analysis reveals a characteristic dihedral angle in the GATA4-targeted compounds that causes stem cell toxicity and thus helps to direct further drug development efforts towards non-toxic derivatives.

A New Series of 1,3,4-Oxadiazole Linked Quinolinyl-Pyrazole/Isoxazole Derivatives: Synthesis and Biological Activity Evaluation

Abstract: A series of 1,3,4-oxadiazole bridged pyrazole/isoxazole bearing quinoline derivatives has been designed and synthesized by a clean and convenient method. Structures of the newly synthesized compounds have been confirmed by FTIR, 1H and 13C NMR, and HRMS spectral data. The titled compounds have been evaluated for their molecular docking guided antimicrobial and anti-inflammatory activity. One of 1,3,4-oxadiazole bridged quinolinyl-pyrazole derivatives has interacted efficiently with E. Coli protein (PDB file: 1KZN), and has been characterized by good antimicrobial activity against the majority of the tested pathogens. Another product has exhibited excellent anti-inflammatory activity.

Design, synthesis and in vitro biological evaluation of isoxazol-4-carboxa piperidyl derivatives as new anti-influenza A agents targeting virus nucleoprotein

Influenza infection is a major cause of morbidity and mortality during seasonal epidemics and sporadic pandemics. It is important and urgent to develop new anti-influenza agents with a new mechanism of action. Nucleozin has been reported as a potent antagonist of nucleoprotein accumulation in the nucleus. In this study, a new series of isoxazol-4-carboxa piperidyl derivatives 1a-j were synthesized and their chemical structures were confirmed by 1H, 13C NMR and mass spectral data. Furthermore, all the synthesized compounds were evaluated for in vitro anti-influenza virus activity against influenza virus (A/PR/8/34 H1N1). Among all the compounds, 1a, 1b, 1c, 1f and 1g exhibited more potent activity than the standard drug, and compound 1b has showed most promising anti-influenza virus activity. These results are also consistent with the docking study results in terms of the design of compounds targeting influenza A via viral nucleoprotein.

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.

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).

Identification, synthesis and photo-protection evaluation of arylthiazole derivatives as a novel series of sunscreens

A novel series of arylthiazole derivatives have been designed, synthesized and evaluated in preventing keratinocytes cell (HaCaT) from UVB exposure induced cellar damage. The structure-activity relationship (SAR) was discussed. More importantly, compound 5a significantly protected the dorsal skin of BALB/c-nu mice against UVB-induced decrustation in vivo. The in vitro and in vivo data for these arylthiazole derivatives suggest further studies for their potential use as photo-protection agents as well as sunscreen candidates.

IMPROVED PROCESS FOR PREPARING PENICILLINS AND INTERMEDIATE COMPOUNDS

Disclosed is an improved process for the preparation of isoxazolyl penicillins of formula (I), wherein X1 and X2 can be independently selected from the group comprising hydrogen, chlorine or fluorine, and its pharmaceutically suitable salts. The process is economic in -situ synthetic method without isolation of any intermediate. (I).

Chiral Mercaptoacetamides Display Enantioselective Inhibition of Histone Deacetylase6 and Exhibit Neuroprotection in Cortical Neuron Models of Oxidative Stress

Mercaptoacetamide-based ligands have been designed as a new class of histone deacetylase (HDAC) inhibitors for possible use in the treatment of neurodegenerative diseases. The thiol group of these compounds provides a key binding element for interaction with the catalytic zinc ion, and thus differs from the more typically employed hydroxamic acid based zinc binding groups. Herein we disclose the chemistry and biology of some substituted mercaptoacetamides with the intention of increasing HDAC6 isoform selectivity while maintaining potency similar to their hydroxamic acid analogues. The introduction of a stereocenter α to the thiol group was found to have a considerable impact on HDAC inhibitor potency. These new compounds were also profiled for their therapeutic potential in an invitro model of stress-induced neuronal injury and were found to act as nontoxic neuroprotective agents.

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).

ANTIVIRAL COMPOUNDS AND METHODS OF MAKING AND USING THERE OF CROSS REFERENCE TO RELATED APPLICATIONS

Compounds which exhibit antiviral activity, particularly against influenza virus,and methods of making and using there of are described herein. In one embodiment, the compounds are heterocyclic amides containing piperazine and isozazole rings and optionally substituted with one or more substituents. The compounds can be formulated with one or more pharmaceutically acceptable excipients to form compositions suitable for enteralor parenteral administration. The compounds are preferably used to treat or prevent Influenza Ainfections, such as H1N1, H2N2, H3N2, H5N1, H7N7, H1N2, H9N2, H7N2, H7N3, and H10N7.