345967-78-4

Basic information

• Product Name: [3-(2-METHOXY-PHENYL)-ISOXAZOL-5-YL]-METHANOL
• Synonyms: [3-(2-METHOXY-PHENYL)-ISOXAZOL-5-YL]-METHANOL
• CAS NO: 345967-78-4
• Molecular Formula: C₁₁H₁₁NO₃
• Molecular Weight: 205.21
• Mol File: 345967-78-4.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: [3-(2-METHOXY-PHENYL)-ISOXAZOL-5-YL]-METHANOL(CAS DataBase Reference)
• NIST Chemistry Reference: [3-(2-METHOXY-PHENYL)-ISOXAZOL-5-YL]-METHANOL(345967-78-4)
• EPA Substance Registry System: [3-(2-METHOXY-PHENYL)-ISOXAZOL-5-YL]-METHANOL(345967-78-4)

Safety Data

• Hazard Codes: Xn
• Statements: 22
• WGK Germany: 3
• Hazardous Substances Data: 345967-78-4(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Research:
[3-(2-METHOXY-PHENYL)-ISOXAZOL-5-YL]-METHANOL is used as a potential drug candidate for its potential therapeutic effects in various diseases and conditions. Its unique structure and properties make it a valuable building block in the synthesis of other molecules with potential biological activity.
Used in Chemical Compound Development:
[3-(2-METHOXY-PHENYL)-ISOXAZOL-5-YL]-METHANOL is used as a key ingredient in the development of new pharmaceuticals and chemical compounds, contributing to the advancement of medical and chemical research.

Upstream product

• 74467-01-9 2-methoxybenzohydroximoyl chloride 
• 107-19-7 propargyl alcohol 
• 29577-53-5 2-Methoxy-benzaldehyde oxime 
• 135-02-4 ortho-anisaldehyde 
• 6175-54-8 hydroxy-1-propyne 

Downstream Products

• 808740-33-2 3-(2-methoxyphenyl)-isoxazole-5-carbaldehyde 
• 1337539-50-0 C₂₇H₃₄N₄O₂ 
• 886364-40-5 3-(2-methoxyphenyl)-5-bromomethylisoxazole 

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.

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.

A rapid and efficient solvent-free microwave-assisted synthesis of pyrazolone derivatives containing substituted isoxazole ring

An efficient synthesis of 4-substituted pyrazolone derivatives was developed. 4-Substituted pyrazolone derivatives were synthesized in 78-97% yields starting from various 3-substituted isoxazole-5-carbaldehydes, ethyl acetoacetate and hydrazine under micr

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.

Efficient solvent-free synthesis of bis(indolyl)methanes on SiO2 solid support under microwave irradiation

An efficient synthesis of bis(indolyl)methanes was developed. Bis(indolyl)methanes were synthesized starting from various aromatic aldehydes with indole under microwave irradiation and solvent-free conditions (85-98 %). Solid support SiO2 was found to possess favorable catalytic and dispersancy parameters for the condensation reaction. Moreover, novel bis(indolyl)methanes containing an isoxazole ring were synthesized via this method in excellent yields (> 94 %) using 3-substituted isoxazole-5-carbaldehydes and indole.

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.

One-pot synthesis of (3-phenylisoxazol-5-yl) methanol derivatives under ultrasound

An ultrasonic-assisted, one-pot, efficient, convenient procedure for the synthesis of (3-phenylisoxazol-5-yl)methanol derivatives has been developed. (3-Phenylisoxazol-5-yl)-methanol derivatives with biological and pharmaceutical property have been synthe

Concise synthesis and antimicrobial activities of new substituted 5-isoxazolpenicillins

The synthesis of a series of new 5-isoxazolpenicillins is described, which were obtained by coupling substituted isoxazoles with 6-APA. Concise large-scale synthesis of 3,5-disubstituted isoxazoles by 1,3-dipolar cycloaddition using copper(I) as catalyst was also investigated. Representative compounds were assayed for antimicrobial activities, showing satisfactory antimicrobial activities against Gram-negative bacteria.

Synthesis and biological evaluation of novel T-type Ca2+ channel blockers

A small molecule library of piperazinylalkylisoxazole derivatives containing about 600 compounds was designed, synthesized and evaluated for blocking effects on T-type Ca2+ channel. Several ligands were identified to possess high inhibitory activity against the T-type Ca 2+ channel. The compound 21 with trifluoromethyl substituents at C3-position of phenyl group (R1) and C2- position of phenyl group (R2) showed the highest inhibitory activity with IC50 value of 1.02μM, which is comparable to that of mibefradil.