39499-34-8

Usage

Uses

Used in Pharmaceutical Industry:
5-METHYLISOXAZOLE-3-CARBONYL CHLORIDE is used as a reagent for the synthesis of pharmaceuticals, contributing to the development of new drugs by introducing the 5-methylisoxazole-3-carbonyl moiety into their molecular structures. This functionality can enhance the pharmacological properties of the resulting compounds, such as potency, selectivity, and bioavailability.
Used in Agrochemical Industry:
In the agrochemical sector, 5-METHYLISOXAZOLE-3-CARBONYL CHLORIDE is employed as a key intermediate in the production of agrochemicals. Its incorporation into the molecular structures of these chemicals can improve their effectiveness in pest control and crop protection, as well as their environmental stability.
Used in Fine Chemicals Synthesis:
5-METHYLISOXAZOLE-3-CARBONYL CHLORIDE is used as a building block in the synthesis of fine chemicals, which are high-purity chemicals used in various applications, including fragrances, dyes, and specialty chemicals. Its introduction into these molecules can enhance their performance characteristics, such as stability, solubility, and reactivity.
Used in Heterocyclic Compounds Synthesis:
5-METHYLISOXAZOLE-3-CARBONYL CHLORIDE is utilized as a precursor in the synthesis of heterocyclic compounds, which are an important class of organic compounds with diverse applications in pharmaceuticals, materials science, and organic synthesis. The introduction of the 5-methylisoxazole-3-carbonyl group into these heterocyclic structures can impart unique properties and reactivity, expanding their potential applications.
Used in Organic Building Blocks:
As an organic building block, 5-METHYLISOXAZOLE-3-CARBONYL CHLORIDE is employed in the construction of complex organic molecules. Its reactivity allows for the formation of various functional groups and structural motifs, which can be further elaborated upon in subsequent synthetic steps, leading to the creation of novel compounds with potential applications in various fields.

InChI:InChI=1/C5H4ClNO2/c1-3-2-4(5(6)8)7-9-3/h2H,1H3

Upstream product

• 85392-50-3 5-methyl-isoxazole-3-carboxylic acid; sodium salt 
• 3405-77-4 5-methylisoxazole 3-carboxylic acid 
• 3209-72-1 ethyl 5-methylisoxazole-3-carboxylate 

Downstream Products

• 74531-16-1 5-methyl-isoxazole-3-carboxylic acid dimethylamide 
• 99984-65-3 5-methyl-3-(N-phenylcarbamoyl)isoxazole 
• 3445-52-1 5-methyl-isoxazole-3-carbothioic acid amide 
• 17605-91-3 3,5-dimethyl-1-(5-methyl-isoxazole-3-carbonyl)-1H-pyrazole 
• 145440-94-4 5-Methyl-isoxazole-3-carboxylic acid (2-methyl-6-nitro-phenyl)-amide 
• 130403-20-2 5-Methyl-isoxazole-3-carboxylic acid (4-bromo-2,6-dimethyl-phenyl)-amide 
• 130403-04-2 5-Methyl-isoxazole-3-carboxylic acid (2,6-diisopropyl-phenyl)-amide 
• 130403-15-5 5-Methyl-isoxazole-3-carboxylic acid (4-methoxy-2,6-dimethyl-phenyl)-amide 
• 145440-87-5 5-Methyl-isoxazole-3-carboxylic acid (2-benzyl-phenyl)-amide 
• 145440-92-2 3-Methyl-2-[(5-methyl-isoxazole-3-carbonyl)-amino]-benzoic acid ethyl ester 
• 130403-03-1 3-(2-methyl 6-isopropyl phenylcarbamoyl)-5-methyl isoxazole 
• 145440-91-1 5-Methyl-isoxazole-3-carboxylic acid (3-bromo-2,6-dimethyl-phenyl)-amide 
• 145441-06-1 5-Methyl-isoxazole-3-carboxylic acid 2,6-dimethyl-phenyl ester 
• 88812-95-7 5-Methyl-isoxazole-3-carboxylic acid (2-methoxy-phenyl)-amide 

Relevant academic research and scientific papers

Isoxazole formamido-4 (3H)-quinazolinone derivative as well as synthesis method and application thereof

The invention relates to a 6-(isoxazolyl-3-formamido)-4 (3H)-quinazolinone derivative as well as a synthesis method and application thereof, belongs to the technical field of medicines, and relates to a general formula (I) in which R1, R2 and R3 are different substituent groups. The invention discloses structures and synthesis methods of the compounds, inhibitory activity of acetylcholin esterase and inhibitory activity of protein tyrosine phosphatase, and the compounds can be further developed into drugs for treating Alzheimer's disease.

THERAPEUTIC COMPOUNDS

The present invention relates to compounds that are Nrf2 activators. The compounds have the structural formula I defined herein. The present invention also relates to processes for the preparation of these compounds, to pharmaceutical compositions comprising them, and to their use in the treatment of diseases or disorders associated with Nrf2 activation.

NOVEL COMPOUNDS AND USES

The present invention relates to compounds of formula (I): wherein Q is O or S; R1 is a cyclic group substituted with at least one group X, wherein R1 may optionally be further substituted; X is any group comprising a carbonyl group; and R2 is a cyclic group substituted at the α-position, wherein R2 may optionally be further substituted. The present invention further relates to salts, solvates and prodrugs of such compounds, to pharmaceutical compositions comprising such compounds, and to the use of such compounds in the treatment and prevention of medical disorders and diseases, most especially by the dual action of NLRP3 inhibition and the stimulation of insulin secretion.

The new compound and its in the treatment of inflammation or inflammation-related application (by machine translation)

The present invention provides novel compounds and their use in the treatment of inflammation or inflammation-related diseases of application, in particular, the invention synthesizes a series of UTLOH compound, the compound can be effectively inhibit LPS-induced PGE2 and NO level, but also can be effective for the treatment of inflammation or inflammation-related disease, particularly for the treatment of Gout, analgesic and anti-inflammatory related diseases. (by machine translation)

4-Iminooxazolidin-2-one as a Bioisostere of the Cyanohydrin Moiety: Inhibitors of Enterovirus 71 3C Protease

A recently reported potent inhibitor of enterovirus 71 3C protease, (R)-1, was found to have stability and potential toxicity issues due to the presence of a cyanohydrin moiety. Modifying the labile cyanohydrin moiety, by serendipity, led to the discovery of 4-iminooxazolidin-2-one-based inhibitors 4e and 4g with potent inhibitory activity and significantly improved stability. In vivo pharmacokinetic studies of 4e also demonstrated high plasma exposure and moderate half-life. These compounds have shown potential of becoming anti-EV71 drug candidates.

Sulfonylureas as Concomitant Insulin Secretagogues and NLRP3 Inflammasome Inhibitors

Insulin-secretory sulfonylureas are widely used, cost-effective treatments for type 2 diabetes (T2D). However, pancreatic β-cells are continually depleted as T2D progresses, thereby rendering the sulfonylurea drug class ineffective in controlling glycaemia. Dysregulation of the innate immune system via activation of the NLRP3 inflammasome, and the consequent production of interleukin-1β, has been linked to pancreatic β-cell death and multiple inflammatory complications of T2D disease. One proposed strategy for treating T2D is the use of sulfonylurea insulin secretagogues that are also NLRP3 inhibitors. We report the synthesis and biological evaluation of nine sulfonylureas that inhibit NLRP3 activation in murine bone-marrow- derived macrophages in a potent, dose-dependent manner. Six of these compounds inhibited NLRP3 at nanomolar concentrations and can also stimulate insulin secretion from a murine pancreatic cell line (MIN6). These novel compounds possess unprecedented dual modes of action, paving the way for a new generation of sulfonylureas that may be useful as therapeutic candidates and/or tool compounds in T2D and its associated inflammatory complications.

Discovery, design and synthesis of a selective S1P3 receptor allosteric agonist

Potent and selective S1P3 receptor (S1P3-R) agonists may represent important proof-of-principle tools used to clarify the receptor biological function and assess the therapeutic potential of the S1P 3-R in cardiovascular, inflammatory and pulmonary diseases. N,N-Dicyclohexyl-5-propylisoxazole-3-carboxamide was identified by a high-throughput screening of MLSMR library as a promising S1P3-R agonist. Rational chemical modifications of the hit allowed the identification of N,N-dicyclohexyl-5-cyclopropylisoxazole-3-carboxamide, a S1P3-R agonist endowed with submicromolar activity and exquisite selectivity over the remaining S1P1,2,4,5-R family members. A combination of ligand competition, site-directed mutagenesis and molecular modeling studies showed that the N,N-dicyclohexyl-5-cyclopropylisoxazole-3-carboxamide is an allosteric agonist and binds to the S1P3-R in a manner that does not disrupt the S1P3-R-S1P binding. The lead molecule herein disclosed constitutes a valuable pharmacological tool to explore the molecular basis of the receptor function, and provides the bases for further rational design of more potent and drug-like S1P3-R allosteric agonists.

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).

Novel tetrahydropyrido[1,2-a]isoindolone derivatives (valmerins): Potent cyclin-dependent kinase/glycogen synthase kinase 3 inhibitors with antiproliferative activities and antitumor effects in human tumor xenografts

The development of CDK and GSK3 inhibitors has been regarded as a potential therapeutic approach, and a substantial number of diverse structures have been reported to inhibit CDKs and GSK-3β in recent years. Only a few molecules have gone through or are currently undergoing clinical trials as CDK and GSK inhibitors. In this paper, we prepared valmerins, a new family containing the tetrahydropyrido[1,2-a]isoindone core. The fused heterocycle was prepared with a straightforward synthesis that was functionalized by a (het)arylurea. Twelve valmerins inhibited the CDK5 and GSK3 with an IC50 100 nM. A semiquantitative kinase scoring was realized, and a cellular screening was done. At the end of our study, we investigated the in vivo potency of one valmerin. Mice exhibited good tolerance to our lead, which proved its efficacy and clearly blocked tumor growth. Valmerins appear also as good candidates for further development as anticancer agents.

Optimization of a series of dipeptides with a P3 β-neopentyl asparagine residue as non-covalent inhibitors of the chymotrypsin-like activity of human 20S proteasome

Inhibition of the proteasome by covalent inhibitors is a clinically proven anti-cancer therapy. We report here that dipeptides with a P3 neopentyl Asn residue are potent, reversible, non-covalent inhibitors selective for the chymotryptic activity of the 20S proteasome in vitro and in cells. The X-ray structure of compound 20 in complex with yeast 20S reveals the importance of hydrophobic bonding interactions of the neopentyl group within the S3 binding pocket of the 20S β5 sub-unit. Four compounds show comparable potencies to boronic acid inhibitors in a panel of assays.