206055-89-2

Basic information

• Product Name: [3-(4-FLUORO-PHENYL)-ISOXAZOL-5-YL]-METHANOL
• Synonyms: [3-(4-FLUORO-PHENYL)-ISOXAZOL-5-YL]-METHANOL;5-isoxazolemethanol, 3-(4-fluorophenyl)-;Albb-009791;[3-(4-Fluorophenyl)-1,2-oxazol-5-yl]methanol;[3-(4-fluorophenyl)-5-isoxazolyl]methanol;[3-(4-Fluoro-phenyl)-isoxazol-5-yl]-
• CAS NO: 206055-89-2
• Molecular Formula: C₁₀H₈FNO₂
• Molecular Weight: 193.17
• Mol File: 206055-89-2.mol

Chemical Properties

• Boiling Point: 358.46 °C at 760 mmHg
• Flash Point: 170.591 °C
• Appearance: /
• Density: 1.299 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.554
• Storage Temp.: Sealed in dry,Room Temperature
• CAS DataBase Reference: [3-(4-FLUORO-PHENYL)-ISOXAZOL-5-YL]-METHANOL(CAS DataBase Reference)
• NIST Chemistry Reference: [3-(4-FLUORO-PHENYL)-ISOXAZOL-5-YL]-METHANOL(206055-89-2)
• EPA Substance Registry System: [3-(4-FLUORO-PHENYL)-ISOXAZOL-5-YL]-METHANOL(206055-89-2)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 206055-89-2(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Research and Development:
[3-(4-Fluoro-phenyl)-isoxazol-5-yl]-methanol is utilized as a key intermediate in the synthesis of various drugs and bioactive molecules. Its distinctive structure and functional groups contribute to the design and creation of novel pharmaceutical compounds with potential therapeutic applications.
Used in Organic Synthesis:
In the field of organic synthesis, [3-(4-Fluoro-phenyl)-isoxazol-5-yl]-methanol serves as a valuable building block, facilitating the construction of complex organic molecules with specific biological activities.
Used in Material Science:
[3-(4-Fluoro-phenyl)-isoxazol-5-yl]-methanol may also find applications in material science, where its versatile reactivity and properties could be harnessed to develop new materials with unique characteristics.
Used in Agrochemicals:
Due to its potential reactivity and properties, [3-(4-Fluoro-phenyl)-isoxazol-5-yl]-methanol could be explored for use in agrochemicals, potentially leading to the development of new compounds for agricultural applications.

InChI:InChI=1/C10H8FNO2/c11-8-3-1-7(2-4-8)10-5-9(6-13)14-12-10/h1-5,13H,6H2

Upstream product

• 459-23-4 4-fluorobenzaldoxime 
• 6175-54-8 hydroxy-1-propyne 
• 31686-94-9 ethyl 4-(4-fluorophenyl)-2,4-dioxobutanoate 
• 403-42-9 1-(4-fluorophenyl)ethanone 
• 377052-00-1 ethyl 3-(4-fluorophenyl)isoxazole-5-carboxylate 
• 107-19-7 propargyl alcohol 
• 459-57-4 4-fluorobenzaldehyde 
• 753479-66-2 [3-(4-fluorophenyl)isoxazol-5-yl]methyl acetate 
• 459-23-4 (E)-4-fluorobenzaldehyde oxime 
• 42202-95-9 4-fluoro-N-hydroxybenzimidoyl chloride 

Downstream Products

• 618383-48-5 3-(4-fluorophenyl)-1,2-oxazole-5-carboxylic acid 
• 1325228-73-6 C₁₂H₉ClFNO₃ 
• 1325228-75-8 C₁₀H₇ClFNO₂ 
• 1239576-23-8 4-chloro-3-(4-fluorophenyl)isoxazole-5-carboxylic acid 
• 1239576-09-0 4-chloro-3-(4-fluorophenyl)-N-((1R,3S)-3-hydroxycyclohexyl)isoxazole-5-carboxamide 
• 1421869-55-7 C₂₅H₂₉FN₄O*ClH 
• 1421869-67-1 C₂₅H₂₈ClFN₄O*ClH 
• 1421869-73-9 C₂₅H₂₈ClFN₄O*ClH 
• 1421869-79-5 C₂₆H₃₁FN₄O₂*ClH 
• 1421869-85-3 C₂₅H₂₈F₂N₄O*ClH 
• 1421869-91-1 C₃₂H₃₃F₃N₄O*ClH 
• 1421869-97-7 C₂₇H₃₃FN₄O*ClH 
• 1421870-03-2 C₂₅H₂₈ClFN₄O*ClH 
• 251912-65-9 3-(4-fluorophenyl)isoxazole-5-carbaldehyde 

Relevant articles and documents

Synthesis of novel 5-(3-alkylquinolin-2-yl)-3-aryl isoxazole derivatives and their cytotoxic activity

The propargyl alcohol on reaction with aldoxime and NaOCl in DCM gave exclusively (3-arylisoxazol-5-yl) methanol 1. The compound 1 was oxidized to an aldehyde 2 followed by reaction with aniline resulted in Schiff's base 3. The compounds 3 were further re

Synthesis and in vitro biological evaluation of novel coumarin derivatives containing isoxazole moieties on melanin synthesis in B16 cells and inhibition on bacteria

A novel series of coumarin derivatives 6a–o, bearing isoxazole moieties were designed and synthesized. After that, they were evaluated for melanin synthesis in murine B16 cells and inhibitory effect on the growth of CA (Candida albicans), EC (Escherichia coli), SA (Staphylococcus aureus). It was found that eleven compounds (6b–f, 6j–o) showed a better activity on melanin synthesis than positive control (8-MOP). Among them, compounds 6d (242%) and 6f (390%), with nearly 1.6 and 2.6-fold potency compared with 8-MOP (149%) respectively, were recognized as the most promising candidate hits for further pharmacological study of anti-vitiligo. Seven halogen substituted compounds exhibited moderate antimicrobial activity against CA. It is interesting that 6e–f and 6l–m, which had two halogens on the benzene showed a comparable activity with Amphotericin B against CA. The evaluation of melanin synthesis in B16 cells and inhibitory effect on bacteria of above structurally diverse derivatives had also led to an outline of structure-activity relationship.

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.

Coumarin phenyl isoxazole derivatives and applications thereof

The invention relates to coumarin phenyl isoxazole derivatives and applications thereof. 4'-hydroxyl chalcone is taken as the raw materials. 4'-hydroxyl chalcone reacts with bromomethyl isoxazole with different substituent groups in the presence of potass

Design and synthesis of a new series of 3,5-disubstituted isoxazoles active against Trypanosoma cruzi and Leishmania amazonensis

Chagas disease and leishmaniasis are neglected tropical diseases (NTDs) endemic in developing countries. Although there are drugs available for their treatment, efforts on finding new efficacious therapies are continuous. The natural lignans grandisin (1)

Preparation method and application of phenylisoxazole-containing chalcone derivatives

The invention relates to a preparation method and application of phenylisoxazole-containing chalcone derivatives. The compounds are prepared by enabling 4'-hydroxyl-chalcone as a raw material to react with different 3-substituted-5-bromomethyl isoxazole under the catalysis of potassium carbonate. The functions of the novel compounds on activity of tyrosinase in a cell-free system and synthesis of melanin in a cell system are also studied. The test results show that compounds 1, 2, 4, 6, 9 and 15 have relatively good tyrosinase agonist activity which is superior to that of a positive control 8-methoxy-psoralen (8-MOP); compounds 1, 2, 4, 5, 7, 9, 11, 15, 16, 17 and 18 can promote synthesis of melanin in B16 mouse cells, and the activity of the compounds is also superior to that of the positive control 8-MOP. The method is gentle in reaction condition and simple and convenient in test step. The phenylisoxazole-containing chalcone derivatives, 1, 2, 4, 5, 6, 7, 9, 11, 15, 16, 17 and 18 prepared by using the method provided by the invention can be all used to prepare medicines for clinically treating leucoderma.

Synthesis and bioactivity of novel isoxazole chalcone derivatives on tyrosinase and melanin synthesis in murine B16 cells for the treatment of vitiligo

A new series of chalcone derivatives 1–18, bearing isoxazole moieties were designed and synthesized, and biologically evaluated for their activity on mushroom tyrosinase and melanin synthesis in murine B16 cells. The result indicated that most of prepared compounds 1–18 showed potent activating effect on tyrosinase, especially for 1–2, 4, 6–7, 9 and 15. Among them, compounds 2, 4 and 9 demonstrated the best activity with EC50?=?1.3, 2.5 and 3.0?μmol·L?1respectively, much better than the positive control 8-methoxypsoralan (8-MOP, EC50?=?14.8?μmol·L?1); In B16 cells, all the tested compounds exhibited a stronger activity on melanogenesis than 8-MOP (with the value of 115%). It was interesting that derivatives substituted with halogen (1, 2, 4, 5, 7, 9) were generally more potent. Compounds 2 (463%) and 18 (438%) with 3 and 4-fold potency compared with 8-MOP respectively, were recognized as the most promising candidate hits for further pharmacological study of anti-vitiligo.

Synthesis of (Z)-(arylamino)-pyrazolyl/isoxazolyl-2-propenones as tubulin targeting anticancer agents and apoptotic inducers

A new class of pyrazole and isoxazole conjugates were synthesized and evaluated for their cytotoxic activity against various human cancer cell lines. These compounds have shown significant cytotoxicity with lower IC50 values. FACS results revealed that A549 cells treated with these compounds arrested cells at the G2/M phase of the cell cycle apart from activating cyclin B1 protein levels. Particularly, compounds 9a and 9b demonstrated a remarkable inhibitory effect on tubulin polymerization and showed a pronounced inhibitory effect on tubulin polymerization with IC50 values of 1.28 μM and 0.28 μM respectively, whereas nocodazole, a positive control, has shown lower antitubulin activity with an IC50 value of 2.64 μM. Furthermore, these compounds induced apoptosis by loss of mitochondrial membrane potential, propidium iodide (PI) staining and the activation of caspase-3. Results of a fluorescence based competitive colchicine binding assay suggest that these conjugates bind successfully at the colchicine binding site of tubulin. These investigations reveal that such conjugates containing pyrazole with a trimethoxy phenyl ring and indole moieties have potential for the development of newer chemotherapeutic agents. This journal is

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.