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Usage

Uses

Used in Pharmaceutical Industry:
5-Methylisoxazole-3-carboxylic acid is used as a reactant for Click/aza-Michael or Click/oligomeric alkyl carbodiimide esterification reactions, which are crucial in the synthesis of various pharmaceutical compounds.
Used in Anticancer Applications:
In the field of oncology, 5-Methylisoxazole-3-carboxylic acid is used as a reactant for the preparation of aminopyrazole amide derivatives. These derivatives act as Raf kinase inhibitors, playing a significant role in the treatment of melanoma cells.
Used in Synthesis of Heterocycle-Bearing Polyfunctionalized Pyrroles:
5-Methylisoxazole-3-carboxylic acid is also utilized in the preparation of trifluoromethoxyphenyl(thiazolyl)pyrroles and other heterocycle-bearing polyfunctionalized pyrroles. These compounds are essential in the development of new drugs and materials with diverse applications.
Used in Chemical Synthesis:
As a versatile reactant, 5-Methylisoxazole-3-carboxylic acid is employed in various chemical synthesis processes, contributing to the development of new compounds and materials with potential applications in different industries.

InChI:InChI=1/C5H5NO3/c1-3-2-4(5(7)8)6-9-3/h2H,1H3,(H,7,8)

Upstream product

• 35166-33-7 (5-methyl-isoxazol-3-yl)-methanol 
• 24068-54-0 3-acetyl-5-methylisoxazole 
• 5699-58-1 2,4-dioxo-pentanoic acid 
• 110-13-4 2,5-hexanedione 
• 615-79-2 ethyl 2,4-diketopentanoate 
• 300-87-8 3,5-dimethyl-1,2-oxazole 
• 7803-49-8 hydroxylamine 
• 3209-72-1 ethyl 5-methylisoxazole-3-carboxylate 
• 20577-61-1 methyl 2,4-dioxopentanoate 
• 27144-54-3 5-methyl-isoxazole-3-carboxylic acid methylamide 

Downstream Products

• 23340-25-2 α-benzal-β-ketobutyronitrile 
• 1131-18-6 1-Phenyl-3-methyl-5-aminopyrazole 
• 10199-57-2 5-methyl-1-phenyl-1H-pyrazole-3-carboxylic acid 
• 80540-92-7 α-acetyl-p-dimethylaminocinnamonitrile 
• 85389-99-7 5-Methyl-isoxazole-3-carboxylic acid {2-[4-(3-cyclohexyl-2-imino-imidazolidine-1-sulfonyl)-phenyl]-ethyl}-amide 
• 39499-34-8 5-methyl-3-isoxazolyl chloride 
• 4857-42-5 3-methyl-5-isoxazolecarboxylic acid 
• 869494-42-8 (E)-(S)-4-{(2R,4S,5S)-2-Benzyl-4-(tert-butyl-dimethyl-silanyloxy)-6-methyl-5-[(5-methyl-isoxazole-3-carbonyl)-amino]-heptanoylamino}-5-((S)-2-oxo-pyrrolidin-3-yl)-pent-2-enoic acid ethyl ester 
• 960225-75-6 5-methyl-4-nitro-1,2-oxazole-3-carboxylic acid 
• 173305-19-6 N-methoxy-N,5-dimethylisoxazole-3-carboxamide 

Relevant academic research and scientific papers

The first coordination compound with 5-methylisoxazole-3-carboxylate: Synthesis and structural characterization of [Cu(L2)(H2O)] ... H2O

The title compound, aquabis(5-methylisoazole-3-carboxylato-O,N)copper(II) monohydrate, [Cu(L2)(H2O)] ... H2O is synthesized and characterized by X-ray diffraction, elementary analysis, and IR. The ligand coordinates to the

A new class of phenylhydrazinylidene derivatives as inhibitors of Staphylococcus aureus biofilm formation

In the struggle against the emergence of the antibiotic resistance, new molecules targeting biofilm formation could be useful as adjuvant of conventional antibiotics. This study focused on a new class of 2-phenylhydrazinylidene derivatives as antivirulence agents. The compound 12e showed interesting activities against biofilm formation of all tested Staphylococcus aureus strains with IC50 ranging from 1.7 to 43 μM; compounds 12f and 13a resulted strong inhibitors of S. aureus ATCC 6538 and ATCC 29213 biofilm formation with IC50 of 0.9 and 0.8 μM, respectively. A preliminary study on the mechanism of action was carried on evaluating the inhibition of sortase A transpeptidase. Compound 12e resulted not to be toxic at 1 mg/ml by using an in vivo model (the wax moth larva model, Galleria mellonella).

Enaminones 12. An explanation of anticonvulsant activity and toxicity per Linus Pauling's clathrate hypothesis

The x-ray crystal structure of 3-((5-methylisoxazol-3-yl)amino)-5- methylcyclohex-2-enone (12b) and 3-((5-methylisoxazolyl-3-yl)amino)-5,5- dimethylcyclohex-2-enone (12c) were determined and correlated to their anticonvulsant activity in mice and rats. A hypothesis for the toxicity of the analogs are advanced. In addition, a series of 5-methyl-N-(3-oxocyclohex-1-enyl) -isoxazole-3-carboxamides were synthesized and evaluated for anticonvulsant activity. These compounds were compared to the activity of the corresponding amino and aminomethyl enaminones. Additional investigation involved the synthesis and evaluation of a trifluoromethyl analog of the active isoxazole tert-butyl 4-(5-methisoxazol-3-yl-amino)-6-methyl-2-oxo-cyclohex-3-ene carboxylate (4f).

The Boulton-Katritzky rearrangement of isocarboxazid

(Chemical Equation Presented) Isocarboxazid rearranges on heating to 5-acetonyl-2-benzyl-4-hydroxy-1,2,3-triazole in DMF at 150°C, in the ionic liquid, [bmin]HSO4- at 100°C or as a melt at 105°C. This is the first reported example of the Boulton-Katritzky rearrangement of an acyl hydrazide.

2-AMINO-5-SUBSTITUTED PYRIMIDINE INHIBITORS

Compounds having the general structure (A) are provided. The compounds of the invention are capable of inhibiting kinases, such as members of the Src kinase family, Vegfr and various other specific receptor and non-receptor kinases. Formula (I):

Design and synthesis of peptidomimetic severe acute respiratory syndrome chymotrypsin-like protease inhibitors

Design, synthesis, and biological evaluation of peptidomimetic severe acute respiratory syndrome chymotrypsin-like protease (SARS-3CLpro) inhibitors for severe acute respiratory syndrome coronavirus (SARS-CoV) are described. These inhibitors exhibited antiviral activity against SARS-CoV in infected cells in the micromolar range. An X-ray crystal structure of our lead inhibitor (4) bound to SARS-3CLpro provided important drug-design templates for the design of small-molecule inhibitors.

Synthesis and biological evaluation of 3-heterocyclyl-7,8,9,10-tetrahydro- (7,10-ethano)-1,2,4-triazolo[3,4-a]phthalazines and analogues as subtype-selective inverse agonists for the GABAAα5 benzodiazepine binding site

The identification of a novel series of 7,8,9,10-tetrahydro-(7,10-ethano)- 1,2,4-triazolo[3,4-a]phthalazines as GABAAα5 inverse agonists, which have both binding and functional (efficacy) selectivity for the benzodiazepine binding site of α5- over α1-, α2-, and α3-containing GABAA receptor subtypes, is described. Binding selectivity was determined to a large part by the degree of planarity of the fused ring system whereas functional selectivity was dependent on the nature of the heterocycle at the 3-position of the triazolopyridazine ring. 3-Furan and 5-methylisoxazole were shown to be optimal for GABAAα5 functional selectvity. 3-(5-Methylisoxazol-3-yl)-6-(2-pyridyl)methyloxy-1,2,4- triazolo[3,4-a]phthalazine (43) was identified as a full inverse agonist at the GABAAα5 subtype with functional selectivity over the other GABAA receptor subtypes and good oral bioavailability.

Chemical oxidation of an anticonvulsant N-(5'-methylisoxazol-3-yl) 2,6- dimethylbenzamide (D2916)

The new anticonvulsant N-(5'-methylisoxazol-3-yl)-2,6-dimethylbeazamide (D2916), which presents two kinds of methyl groups which could be oxidized, was submitted to various chemical oxidizing agents. Several sites and degrees of oxidation were observed. The main oxidized site was the arylmethyl group without cleavage of the isoxazole ring, leading via carboxylic acid and primary alcohol intermediates to phthalimide and lactame derivatives. In no case was the methyl group of the isoxazole moiety hydroxylated.

Certain triazole compounds and their pharmaceutical uses

In the invention of novel nonsteroidal antiinflammatory compounds the title novel triazole compounds, were synthesized from carboxylic acids, 2,5-acetonylacetone, or isoniazid, respectively. To give 4H-1,2,4-triazol-3-thiols. Treatment of 4H-1,2,4-tri-azol-3-thiols with methyl chloroacetate or methyl α-chloropropionate resulted in the formation of compounds I-VI. The antiinflammatory activity of those new triazole compounds were determined by the carrageenin-induced edema method and they showed potent activity. In the dosage form studies those compounds of formula I-VI were added suituble vehicleo to prepare antiinflammatory agents.

New N-aryl isoxazolecarboxamides and N-isoxazolylbenzamides as anticonvulsant agents

We prepared a series of N-aryl isoxazolecarboxamide, N-isoxazolylbenzamide compounds and derivatives and studied their anticonvulsant action in MES and MMS tests. Some of these reveal considerable activity, especially with respect to MES test. The disubstitution in the 2.6-position on the phenyl ring by two methyl groups would appear to be of primary importance for the activity. The amide bridge between the phenyl and isoxazolic rings, whether of the anilide or benzamide type, seems to show similar anticonvulsant behavior. We have selected the derivatives 8 (N-(2.6-dimethylphenyl)-5-methyl-3-isoxazolecarboxamide, 12 (N-(2.6-dimethylphenyl)-5-hydroxymethyl-3-isoxazolecarboxamide) and 51 (N-(5-methyl-3-isoxazolyl)-2.6-dimethylbenzamide) which are presently being studied in more extended pharmacological tests.