2039-50-1

Usage

Uses

Used in Pharmaceutical Research:
5-(Bromomethyl)-3-phenylisoxazole is used as a chemical intermediate for the synthesis of various pharmaceutical compounds. Its unique chemical properties allow for the creation of complex substances and drug molecules, contributing to the development of new medications.
Used in Chemical Research:
In the field of chemical research, 5-(Bromomethyl)-3-phenylisoxazole serves as a valuable reagent for conducting various organic reactions. Its versatility and unique properties make it suitable for exploring new chemical pathways and reactions, furthering scientific understanding and innovation.
Used in Organic Synthesis:
5-(Bromomethyl)-3-phenylisoxazole is used as a key component in organic synthesis, where it can be incorporated into a wide range of organic molecules. Its presence in the molecular structure can impart specific properties or reactivity, making it a valuable building block for the synthesis of novel compounds.
Used in Drug Development:
In the drug development industry, 5-(Bromomethyl)-3-phenylisoxazole is used as a precursor in the synthesis of potential drug candidates. Its unique structure and reactivity can contribute to the discovery of new therapeutic agents with improved efficacy and selectivity.
Used in Chemical Intermediates Production:
5-(Bromomethyl)-3-phenylisoxazole is utilized as a chemical intermediate in the production of various specialty chemicals. Its unique properties make it a valuable component in the synthesis of advanced materials, dyes, and other chemical products.

InChI:InChI=1/C10H8BrNO/c11-7-9-6-10(12-13-9)8-4-2-1-3-5-8/h1-6H,7H2

Upstream product

• 873-67-6 benzonitrile oxide 
• 106-96-7 propargyl bromide 
• 513-31-5 2-bromoallyl bromide 
• 932-90-1 syn-benzaldehyde oxime 
• 698-16-8 benzohydroximoyl chloride 
• 932-90-1 Benzaldoxime 
• 90924-12-2 3-phenyl-5-hydroxymethylisoxazole 
• 100-52-7 benzaldehyde 
• 622-32-2 (Z)-benzaldehyde oxime 
• 20141-73-5 benzaldehyde oxime O-tributylstannyl ether 

Downstream Products

• 36895-31-5 3-phenyl-5-p-tolyloxymethyl-isoxazole 
• 62679-05-4 5-methylsulfanylmethyl-3-phenyl-isoxazole 
• 36895-33-7 N-[4-(3-phenyl-isoxazol-5-ylmethoxy)-phenyl]-acetamide 
• 1008-74-8 5-methyl-3-phenylisoxazole 
• 90924-12-2 3-phenyl-5-hydroxymethylisoxazole 
• 36821-71-3 N-(3-phenyl-isoxazol-5-ylmethoxy)-phthalimide 
• 36895-36-0 7-((3-phenylisoxazol-5-yl)methoxy)-4-methyl-2H-benzopyran-2-one 
• 35121-45-0 5-naphthalen-2-yloxymethyl-3-phenyl-isoxazole 
• 35121-46-1 5-phenoxymethyl-3-phenyl-isoxazole 
• 103912-66-9 5-2-phenylamidino)aminomethyl>-3-phenyl-isoxazole 
• 1026-60-4 3-phenyl-5-piperidinomethylisoxazole 
• 1245573-80-1 C₁₉H₂₁N₃O₄S 
• 1245573-79-8 C₂₁H₂₅N₃O₄ 
• 54408-35-4 1-(3-phenyl-1,2-oxazol-5-yl)methanamine 

Relevant academic research and scientific papers

A metal-free approach for in situ regioselective synthesis of isoxazoles via 1,3 dipolar cycloaddition reaction of nitrile oxide with propargyl bromide

Herein, we report a multi-component reaction (MCRs) to synthesise a range of 3-phenyl-5-(bromomethyl)isoxazoles analogues using DMF/water mixture as solvent, providing desired products in good to excellent yields. The reaction efficiently involves the 1,3-dipolar cycloaddition reaction between propargyl bromide and in situ-generated α-chloro aldoximes. The protocol proceeded well under mild metal-free conditions and showed a tolerance for a wide range of substituents. Graphical abstract: [Figure not available: see fulltext.]

Product selectivity of thermal Buchner reaction of methyl 2-(3-arylisoxazol-5-yl)-2-diazoacetates with benzene, naphthalene and mesitylene, and ring-opening/closing reaction of products

Methyl 2-(3-arylisoxazol-5-yl)-2-diazoacetates were synthesized and the product selectivity of their thermal Buchner reaction with benzene, naphthalene and mesitylene was studied. The reaction of the isoxazolyl-substituted diazoacetates with benzene gave

CBP/CATENIN SIGNALING PATHWAY INHIBITORS AND USES THEREOF

Provided are compounds of formula (Ia), (Ib) and (IIa), and pharmaceutically acceptable salts thereof. Additionally provided are compositions and pharmaceutical compositions comprising the compounds, therapeutic methods using same for modulating (e.g., inhibiting) CREB binding protein (CBP)/β-catenin mediated signaling in treating a condition, disease or disorder (e.g., fibrosis, cancer, neurological conditions, metabolic disorders (e.g., diabetes, etc.), and skin conditions (dermatitis, psoriasis, scarring, alopecia, etc.) mediated by aberrant CBP/β -catenin signaling, and cosmetic methods for treating skin conditions (e.g., aging, etc.). Additionally provided are methods for enhancing vaccine efficacy using the compounds and compositions. Further provided are methods for efficiently synthesizing a clinical grade drug, comprising use, in a penultimate, or last reaction step under GMP conditions, of an intermediate 2-propynyl-compound to form a clinical grade isoxazole derivative (e.g., via 3+2 cycloaddition).

Facile synthesis and docking studies of 7-hydroxyflavanone isoxazoles and acrylates as potential anti-microbial agents

The present study is aimed to synthesize the novel 7-hydroxyflavanone derived compounds and to assess their biological activity. Two series of compounds such as 2-phenyl-7-((3-phenylisoxazol-5-yl)methoxy)chroman-4-ones (6a–h) and 4-oxo-2-phenylchroman-7-yl acrylates (8a–k) were synthesized from 7-hydroxyflavanone. All the compounds were subjected to anti-microbial activity and molecular docking studies. The results showed that the compounds 6e, 6g–h, 8h–i and 8k were exhibited most potent anti-microbial activity when compared with the standard drugs. Further, the docking studies revealed that the compounds 6a and 8h have the highest binding affinity score of sterol 14-α demethylase and DNA gyrase B respectively. This is the first report assigning unique synthesis of 7-hydroxyflavanone derivatives and their anti-microbial activity proved with in silico studies. Furthermore, the present study is useful for constructive research to synthesize novel compounds along with their biological activity. [Figure not available: see fulltext.].

Synthesis of Isoxazolines and Isoxazoles via Metal-Free Desulfitative Cyclization

A novel, one-pot reaction for the synthesis of isoxazolines and isoxazoles is developed via a cascade process under metal-free conditions. The approach involves the formation of intramolecular C-N and C-O bonds and intermolecular C-C bonds from aromatic alkenes or alkynes and N -hydroxysulfonamides using hypervalent iodine(VII) and iodine as the oxidant. Activation of C-H and C-C bonds/construction of C-O bonds/elimination of SO 2 /C-N bond formation is achieved in sequence in the reaction system.

Synthesis of Halomethyl Isoxazoles/Cyclic Nitrones via Cascade Sequence: 1,2-Halogen Radical Shift as a Key Link

A novel iminoxyl radical-promoted dichotomous regioselective 5-exo-trig cyclization onto vinylic halogen/1,2-halogen radical shift sequence is developed for the synthesis of halomethyl isoxazoles/cyclic nitrones using β-halo-β,?- and ?-halo-?,?-unsaturated ketoximes as the substrates and PhI(OAc)2/TEMPO as the oxidation system. DFT calculations reveal that a halogen-bridged three-membered ring transition state is involved in the 1,2-Cl-/Br-atom shift, while the 1,2-I atom migration can be taken into account with an elimination/readdition mechanism. The migration ability was indicated to be ranked in the following order: I > Br > Cl.

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.

Lead Optimization Generates CYP11B1 Inhibitors of Pyridylmethyl Isoxazole Type with Improved Pharmacological Profile for the Treatment of Cushing's Disease

Cushing's disease, characterized by elevated plasma cortisol levels, can be controlled by inhibition of 11β-hydroxylase (CYP11B1). The previously identified selective and potent CYP11B1 inhibitor 5-((5-methylpyridin-3-yl)methyl)-2-phenylpyridine Ref 7 (IC50= 2 nM) exhibited promutagenic potential as well as very low oral bioavailability in rats (F = 2%) and was therefore modified to overcome these drawbacks. Successful lead optimization resulted in similarly potent and selective 5-((5-methoxypyridin-3-yl)methyl)-3-phenylisoxazole 25 (IC50 = 2 nM, 14-fold selectivity over CYP11B2), exhibiting a superior pharmacological profile with no mutagenic potential. Furthermore, compound 25 inhibited rat CYP11B1 (IC50 = 2 μM) and showed a high oral bioavailability (F = 50%) and sufficient plasma concentrations in rats, providing an excellent starting point for a proof-of-principle study.

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.

TRIAZOLOPYRIDINE AND TRIAZOLOPYRIMIDINE INHIBITORS OF MYELOPEROXIDASE

The present invention provides compounds of Formula (I): wherein A and R1 are each as defined in the specification, and compositions comprising any of such novel compounds. These compounds are myeloperoxidase (MPO) inhibitors and/or eosinophil peroxidase (EPX) inhibitors, which may be used as medicaments.