66033-76-9

Usage

Uses

Used in Organic Synthesis:
1,2-Benzisoxazole, 5-bromo-3-methylis used as a building block in organic synthesis for its unique reactivity and properties that facilitate the creation of complex organic molecules. Its presence in synthetic pathways can lead to the development of novel compounds with specific functionalities.
Used in Pharmaceutical Research:
In the pharmaceutical industry, 1,2-Benzisoxazole, 5-bromo-3-methylis utilized as a key intermediate in the development of new drugs. Its structural features allow for the design of molecules with potential therapeutic effects, contributing to the advancement of medicinal chemistry.
Used in Drug Development:
1,2-Benzisoxazole, 5-bromo-3-methylserves as a valuable asset in drug development, where its specific chemical properties can be leveraged to create pharmaceutical agents with targeted actions. Its role in this process is crucial for the discovery and optimization of new therapeutic agents.

Upstream product

• 42524-21-0 1-(5-bromo-2-hydroxyphenyl)ethan-1-one oxime 
• 1215858-74-4 (Z)-1-(2,5-dibromophenyl)ethanone oxime 
• 92832-02-5 1-(5-bromo-2-hydroxyphenyl)ethanimine 
• 1450-75-5 5-Bromo-2-hydroxyacetophenone 
• 1416157-63-5 (E)-1-(5-bromo-2-hydroxyphenyl)ethanone oxime 
• 1450-72-2 5-methyl-2-hydroxyacetophenone 
• 33598-02-6 2'-hydroxy-5'-methylacetophenone imine 
• 106-41-2 4-bromo-phenol 

Downstream Products

• 478169-74-3 3-methylbenzo[d]isoxazole-5-carboxylic acid 
• 1314136-00-9 3-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzisoxazole 

Relevant academic research and scientific papers

ISOXAZOLINE DERIVATIVES AND THEIR USES IN AGRICULTURE RELATED APPLICATION

The present invention provides isoxazoline derivatives and uses thereof in agriculture; in particular, the present invention provides a compound having formula (I), or a stereoisomer, an N-oxide or a salt thereof, preparation methods thereof, and compositions containing these compounds and uses thereof in agriculture, particularly uses as herbicide active ingredients for controlling unwanted plants; wherein R1, R2, R3, R4, n, R5, R6 and Hy are as described in the invention.

A kind of benzo [d] different wicked zuozuo apperception compound and use thereof

The invention relates to the technical field of chemical medicine, and particularly discloses a benzo[d]isoxazole compound shown as a general formula (A) and application thereof. The compound can effectively inhibit bromodomain of BET family proteins so as to block interaction between the BET family proteins and chromatin histone to adjust genetic transcription, cause changing of a downstream signal path and exert important influence on various diseases, so that the compound and a combination thereof can be used for preparing medicine for treating or preventing diseases like tumorigenesis, inflammation, viral infection, cell proliferation disorder, autoimmune diseases and septicemia.

Derisking the Cu-Mediated 18F-Fluorination of Heterocyclic Positron Emission Tomography Radioligands

Molecules labeled with fluorine-18 (18F) are used in positron emission tomography to visualize, characterize and measure biological processes in the body. Despite recent advances in the incorporation of 18F onto arenes, the development of general and efficient approaches to label radioligands necessary for drug discovery programs remains a significant task. This full account describes a derisking approach toward the radiosynthesis of heterocyclic positron emission tomography (PET) radioligands using the copper-mediated 18F-fluorination of aryl boron reagents with 18F-fluoride as a model reaction. This approach is based on a study examining how the presence of heterocycles commonly used in drug development affects the efficiency of 18F-fluorination for a representative aryl boron reagent, and on the labeling of more than 50 (hetero)aryl boronic esters. This set of data allows for the application of this derisking strategy to the successful radiosynthesis of seven structurally complex pharmaceutically relevant heterocycle-containing molecules.

Method for preparing benzisoxazole in one pot based on 2-hydroxyacetophenone oxime and derivatives thereof

The invention relates to the technical field of medicinal chemistry and in particular discloses a method for preparing benzisoxazole in one pot based on 2-hydroxyacetophenone oxime and derivatives thereof. The preparation method is as follows: under microwave or oil bath heating conditions, in an organic solvent, one-pot inversion is carried out on 2-hydroxyacetophenone oxime and derivatives thereof to form benzisoxazole compounds by utilizing a fluorine-containing accelerator and alkali. The method for synthesizing benzisoxazole has the advantages that raw materials are rich in source and easy to get, synthetic steps are short, the operation is simple and convenient, the product yield is high, and the highest yield is 93%. A benzisoxazole structure exists in multiple drug molecules, so that the novel one-pot synthesis method disclosed by the invention has potential practical values.

Bioavailability Studies and in vitro Profiling of the Selective Excitatory Amino Acid Transporter Subtype 1 (EAAT1) Inhibitor UCPH-102

Although the selective excitatory amino acid transporter subtype 1 (EAAT1) inhibitor UCPH-101 has become a standard pharmacological tool compound for in vitro and ex vivo studies in the EAAT research field, its inability to penetrate the blood-brain barrier makes it unsuitable for in vivo studies. In the present study, per os (p.o.) administration (40 mg kg-1) of the closely related analogue UCPH-102 in rats yielded respective plasma and brain concentrations of 10.5 and 6.67 μm after 1 h. Three analogue series were designed and synthesized to improve the bioavailability profile of UCPH-102, but none displayed substantially improved properties in this respect. In vitro profiling of UCPH-102 (10 μm) at 51 central nervous system targets in radioligand binding assays strongly suggests that the compound is completely selective for EAAT1. Finally, in a rodent locomotor model, p.o. administration of UCPH-102 (20 mg kg-1) did not induce acute effects or any visible changes in behavior. EAAT1 inhibition beyond the BBB: In the present study, oral administration (40 mg kg-1) of the selective excitatory amino acid transporter subtype 1 (EAAT1) inhibitor UCPH-102 in rats yielded respective plasma and brain concentrations of 10.5 and 6.67 μm after 1 h. In vitro profiling of UCPH-102 (10 μm) at 51 central nervous system targets in radioligand binding assays strongly suggests that the compound is fully selective for EAAT1.

BENZOISOXAZOLE-SUBSTITUTED COMPOUNDS AS MGLUR4 ALLOSTERIC POTENTIATORS, COMPOSITIONS, AND METHODS OF TREATING NEUROLOGICAL DYSFUNCTION

Compounds which are useful as allosteric potentiators/positive allosteric modulators of the metabotropic glutamate receptor subtype 4 (mGluR4); synthetic methods for making the compounds; pharmaceutical compositions comprising the compounds; and methods of using the compounds, for example, in treating neurological and psychiatric disorders or other disease state associated with glutamate dysfunction.

Pyrimidine compounds and methods of making and using same

Disclosed herein are pyrimidinyl compounds that are contemplated to be modulators of cystic fibrosis transmembrane regulators (CFTR), and methods of making and using same. Also provided are pharmaceutical compositions and methods of treating disorders associated with cystic fibrosis transmembrane regulators, such as airway inflammation, cystic fibrosis, and the like.

A divergent and selective synthesis of isomeric benzoxazoles from a single N-Cl imine

A divergent and regioselective synthesis of either 3-substituted benzisoxazoles or 2-substituted benzoxazoles from readily accessible ortho-hydroxyaryl N-H ketimines is described. The reaction proceeds in two distinct pathways through a common N-Cl imine intermediate: (a) N-O bond formation to form benzisoxazole under anhydrous conditions and (b) NaOCl mediated Beckmann-type rearrangement to form benzoxazole, respectively. The reaction path also depends on the electronic nature of the aromatic ring, with the electron-rich aromatic rings favoring the rearrangement and the electron-deficient rings favoring the N-O bond formation. A Beckmann-type rearrangement mechanism via net [1,2]-aryl migration for the formation of 2-substituted benzoxazole is proposed.

Copper-catalyzed cyclization of Z-oximes into 3-methyl-1,2-benzisoxazoles

A practical and effective room temperature copper-catalyzed cyclization of Z-oximes is developed. 3-Methyl-1,2-benzisoxazoles are obtained in 58-79% yields. Also, the Z-selective synthesis of o-bromo acetophenone oximes is presented for the first time.

Microwave induced synthesis of 3-substituted 1,2-benzisoxazole derivatives

A rapid, cost-effective and eco-friendly synthesis of 3-substituted 1,2-benzisoxazoles from o-hydroxy ketoximes in solvent free conditions using solid support under microwave irradiation has been achieved.