206055-91-6

Basic information

• Product Name: [3-(4-BROMO-PHENYL)-ISOXAZOL-5-YL]-METHANOL
• Synonyms: [3-(4-BROMO-PHENYL)-ISOXAZOL-5-YL]-METHANOL;[3-(4-bromophenyl)-1,2-oxazol-5-yl]methanol
• CAS NO: 206055-91-6
• Molecular Formula: C₁₀H₈BrNO₂
• Molecular Weight: 254.08
• Mol File: 206055-91-6.mol

Chemical Properties

• Appearance: /
• Storage Temp.: 2-8°C
• CAS DataBase Reference: [3-(4-BROMO-PHENYL)-ISOXAZOL-5-YL]-METHANOL(CAS DataBase Reference)
• NIST Chemistry Reference: [3-(4-BROMO-PHENYL)-ISOXAZOL-5-YL]-METHANOL(206055-91-6)
• EPA Substance Registry System: [3-(4-BROMO-PHENYL)-ISOXAZOL-5-YL]-METHANOL(206055-91-6)

Safety Data

• Hazard Codes: Xn
• Statements: 22
• WGK Germany: 3
• Hazardous Substances Data: 206055-91-6(Hazardous Substances Data)

Usage

Uses

Used in Medicinal Chemistry:
[3-(4-BROMO-PHENYL)-ISOXAZOL-5-YL]-METHANOL is used as a pharmaceutical intermediate for its potential antimicrobial, anti-tumor, and anti-inflammatory properties. The isoxazole ring is known for its bioactivity, making [3-(4-BROMO-PHENYL)-ISOXAZOL-5-YL]-METHANOL a promising candidate for the development of new drugs.
Used in Organic Chemistry:
[3-(4-BROMO-PHENYL)-ISOXAZOL-5-YL]-METHANOL is used as a synthetic precursor for the preparation of other chemical compounds. The bromine atom on the phenyl ring can be utilized in various organic synthesis reactions, such as cross-coupling reactions, to form new functionalized molecules.
Used in Industrial Chemistry:
[3-(4-BROMO-PHENYL)-ISOXAZOL-5-YL]-METHANOL is used as a building block in the synthesis of specialty chemicals and materials. Its unique structure and functional groups can be employed to create new compounds with specific properties for use in various industries, such as pharmaceuticals, agrochemicals, and materials science.
Overall, [3-(4-BROMO-PHENYL)-ISOXAZOL-5-YL]-METHANOL is a versatile chemical compound with potential applications across multiple disciplines, making it a valuable target for further research, development, and synthesis.

Upstream product

• 107-19-7 propargyl alcohol 
• 29203-58-5 4-bromo-N-hydroxybenzenecarboximidoyl chloride 
• 1122-91-4 4-bromo-benzaldehyde 
• 25062-46-8 4-bromobenzaldehyde oxime 

Downstream Products

• 1262439-72-4 N-((3-(4-bromophenyl)isoxazol-5-yl)methyl)propanamide 
• 1262439-73-5 N-((3-(4-bromophenyl)isoxazol-5-yl)methyl)-2-methylpropanamide 
• 1262439-74-6 2-bromo-N-((3-(4-bromophenyl)isoxazol-5-yl)methyl)ethanamide 
• 1262439-61-1 5-(azidomethyl)-3-(4-bromophenyl)isoxazole 
• 1570098-93-9 ferrocenecarboxylic acid 4-([3-(4-bromophenyl)isoxazol-5-yl]methoxy)ester 
• 1620955-30-7 C₃₀H₂₇N₅O₅ 
• 1620955-97-6 (3-(4'-(4-(hydrazinecarbonyl)-1,6-naphthyridin-2-yl)-[1,1'-biphenyl]-4-yl)isoxazol-5-yl)methyl methylcarbamate hydrochloride 
• 1620955-94-3 C₁₂H₁₁BrN₂O₃ 
• 1620955-95-4 C₁₈H₂₃BN₂O₅ 
• 1620955-96-5 C₃₂H₃₀N₆O₆ 
• 1620955-31-8 2-(4'-(5-(hydroxymethyl)isoxazol-3-yl)-[1,1'-biphenyl]-4-yl)-1,6-naphthyridine-4-carbohydrazide hydrochloride 
• 1056456-10-0 5-(methoxymethyl)-3-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)isoxazole 
• 863391-64-4 3-(4-bromophenyl)isoxazole-5-carbaldehyde 

Relevant articles and documents

Ultrasonic-assisted synthesis of 1,4-disubstituted 1,2,3-triazoles via various terminal acetylenes and azide and their quorum sensing inhibition

An efficient synthesis of 1,4-disubstituted 1,2,3-triazole derivatives was studied. 1,4-Disubstituted 1,2,3-triazoles containing isoxazole and thymidine structures were synthesized in 84–96% yields starting from various terminal isoxazole ether alkynes and β-thymidine azide derivatives via a 1,3-dispolar cycloaddition using copper acetate, sodium ascorbate as the catalyst under ultrasonic assisted condition. All the target compounds were characterized by HRMS, FT-IR, 1H NMR and 13C NMR spectroscopy. Furthermore, the quorum sensing inhibitory activities of synthesized compounds were evaluated with Chromobacterium violaceum (C. Violaceum CV026) based on their inhibition of violacein production, with compound C10-HSL as a positive control. The compounds 8a, 8c and 8f exhibited considerable levels of inhibitory activity against violacein production, and IC50 values were 217?±?19, 223?±?20 and 42.8?±?4.5?μM, respectively, which highlighted the potential of these compounds as lead structures for further research towards the development of novel QS inhibitors.

Novel inhibitors of Plasmodium falciparum based on 2,5-disubstituted furans

Phenotypic HTS campaigns with a blood stage malaria assay have been used to discover novel chemotypes for malaria treatment with potential alternative mechanisms of action compared to existing agents. N1-(5-(3-Chloro-4-fluorophenyl)furan-2-yl)-N3,N3-dimethylpropane-1,3-diamine, 1 was identified as a modest inhibitor of P. falciparum NF54 (IC50= 875 nM) with an apparent long plasma half-life after high dose oral administration to mice, although the compound later showed poor metabolic stability in liver microsomes through ring- and side chain-oxidation and N-dealkylation. We describe here the synthesis of derivatives of 1, exploring the influence of substitution patterns around the aromatic ring, variations on the alkyl chain and modifications in the core heterocycle, in order to probe potency and metabolic stability, where 4k showed a long half-life in rats.

Efficient synthesis of bis-isoxazole ethers via 1,3-dipolar cycloaddition catalysed by Zn/Zn2+ and their antifungal activities

An efficient method was developed for synthesising isoxazoles. A series of novel bis-isoxazole ether compounds VI, VII and VIII were synthesised starting from different substituted aldehydes (I) via a 1,3-dispolar cycloaddition using Zn/Zn2+ as a catalyst; these were characterised by FT-IR, HRMS, 1H NMR and 13C NMR spectroscopy. In addition, the antimicrobial properties of the synthesised products were investigated. The synthesised compounds exhibited significant antifungal activities in comparison with the standard drugs, fluconazole and itraconazole. It was found that Candida albicans was sensitive to 2-substituted phenyl bis-isoxazole ethers bearing pyridyl.

METALLOENZYME INHIBITOR COMPOUNDS

The instant invention describes compounds having metalloenzyme modulating activity, and methods of treating diseases, disorders or symptoms thereof mediated by such metalloenzymes.

Discovery, synthesis, and biological evaluation of a novel group of selective inhibitors of filoviral entry

Herein, we report the development of an antifiloviral screening system, based on a pseudotyping strategy, and its application in the discovery of a novel group of small molecules that selectively inhibit the Ebola and Marburg glycoprotein (GP)-mediated infection of human cells. Using Ebola Zaire GP-pseudotyped HIV particles bearing a luciferase reporter gene and 293T cells, a library of 237 small molecules was screened for inhibition of GP-mediated viral entry. From this assay, lead compound 8a was identified as a selective inhibitor of filoviral entry with an IC50 of 30 μM. To analyze functional group requirements for efficacy, a structure-activity relationship analysis of this 3,5-disubstituted isoxazole was then conducted with 56 isoxazole and triazole derivatives prepared using "click" chemistry. This study revealed that while the isoxazole ring can be replaced by a triazole system, the 5-(diethylamino)acetamido substituent found in 8a is required for inhibition of viral-cell entry. Variation of the 3-aryl substituent provided a number of more potent antiviral agents with IC50 values ranging to 2.5 μM. Lead compound 8a and three of its derivatives were also found to block the Marburg glycoprotein (GP)-mediated infection of human cells.

NOVEL PHENYLPROPIONIC ACID DERIVATIVES AS PEROXISOME PROLIFERATOR-ACTIVATED GAMMA RECEPTOR MODULATORS, METHOD OF THE SAME, AND PHARMACEUTICAL COMPOSITION COMPRISING THE SAME

The present invention provides a novel phenylpropionic acid derivative and a PPAR-γ modulator comprising the same as an active ingredient. The phenylpropionic acid derivative of the present invention has modulatory action on function of PPAR-γ and then exhibits hypoglycemic, hypolipidemic and insulin resistance-reducing effects on PPAR-mediated diseases or disorders. Therefore, the present invention is prophylactically or therapeutically effective for diabetes and metabolic diseases.

NOVEL PHENYLPROPIONIC ACID DERIVATIVES AS PEROXISOME PROLIFERATOR-ACTIVATED GAMMA RECEPTOR MODULATORS, METHOD OF THE SAME, AND PHARMACEUTICAL COMPOSITION COMPRISING THE SAME

The present invention provides a novel phenylpropionic acid derivative and a PPAR-γ modulator comprising the same as an active ingredient. The phenylpropionic acid derivative of the present invention has modulatory action on function of PPAR-γ and then exhibits hypoglycemic, hypolipidemic and insulin resistance-reducing effects on PPAR-mediated diseases or disorders. Therefore, the present invention is prophylactically or therapeutically effective for diabetes and metabolic diseases.

Identification of phenylisoxazolines as novel and viable antibacterial agents active against gram-positive pathogens

A new and promising group of antibacterial agents, collectively known as the oxazolidinones and exemplified by linezolid (PNU-100766, marketed as Zyvox), have recently emerged as important new therapeutic agents for the treatment of infections caused by G