14731-10-3

Usage

Uses

Used in Pharmaceutical Industry:
3-(Chloromethyl)-5-phenylisoxazole is used as a synthetic intermediate for the development of new pharmaceutical compounds. Its chloromethyl group and phenylisoxazole ring enable the creation of diverse molecules with potential medicinal properties, contributing to the discovery of innovative treatments and therapies.
Used in Agrochemical Industry:
In the agrochemical sector, 3-(Chloromethyl)-5-phenylisoxazole serves as a key intermediate in the synthesis of various agrochemicals. Its reactivity and structural features facilitate the production of compounds with pesticidal, herbicidal, or other agricultural applications, enhancing crop protection and yield.
Used in Organic Synthesis:
3-(Chloromethyl)-5-phenylisoxazole is utilized as a versatile intermediate in organic synthesis for the introduction of different functional groups into organic compounds. Its unique structure allows chemists to perform a variety of chemical reactions, leading to the formation of new molecules with a range of applications in various industries.

InChI:InChI=1/C10H8ClNO/c11-7-9-6-10(13-12-9)8-4-2-1-3-5-8/h1-6H,7H2

Upstream product

• 1619-37-0 (5-phenylisoxazol-3-yl)methanol 
• 1007401-94-6 (Z)-1,4-dichloro-4-phenylbut-3-en-2-one 
• 6296-54-4 ethyl 2,4-dioxo-4-phenylbutyrate 
• 98-86-2 acetophenone 
• 7063-99-2 ethyl 5-phenylisoxazole-3-carboxylate 
• 98-85-1 1-Phenylethanol 
• 100-52-7 benzaldehyde 
• 59985-82-9 5-phenylisoxazole-3-carbaldehyde 
• 858489-69-7 3-(methoxymethyl)-5-phenylisoxazole 
• 90770-96-0 3-hydroxyiminomethyl-5-phenylisoxazole 

Downstream Products

• 89102-76-1 diethyl [(5-phenyl-1,2-oxazol-3-yl)methyl]phosphonate 
• 1195982-98-9 (R)-3-(1-phenylcycloheptanecarbonyloxy)-1-(5-phenylisoxazol-3-ylmethyl)-1-azoniabicyclo[2.2.2]octane chloride 
• 1195982-93-4 (R)-1-(5-phenylisoxazol-3-ylmethyl)-3-(1-thiophen-2-ylcycloheptanecarbonyloxy)-1-azoniabicyclo[2.2.2]octane chloride 
• 1195983-04-0 (R)-3-(1-phenylcyclopentanecarbonyloxy)-1-(5-phenylisoxazol-3-ylmethyl)-1-azoniabicyclo[2.2.2]octane chloride 
• 1195983-06-2 (R)-3-(1-phenylcyclohexanecarbonyloxy)-1-(5-phenylisoxazol-3-ylmethyl)-1-azoniabicyclo[2.2.2]octane chloride 
• 154016-47-4 (5-phenyl-isoxazol-3-yl)methylamine 
• 1026-63-7 4-[(5-phenylisoxazol-3-yl)methyl]morpholine 

Relevant academic research and scientific papers

Synthesis of Fluorine-Containing Derivatives of 5-Arylisoxazoles and 4,5-Dichlorothiazole

Alkylation of fluorophenols and phenolic aldehydes with 5-phenyl(p-tolyl)-3-chloromethylisoxazole under the Williamson reaction conditions afforded the corresponding ethers. Condensation of the resulting phenolic aldehyde derivatives and 5-phenyl(p-tolyl)

Design, synthesis and structure-based optimization of novel isoxazole-containing benzamide derivatives as FtsZ modulators

Antibiotic resistance among clinically significant bacterial pathogens is becoming a prevalent threat to public health, and new antibacterial agents with novel mechanisms of action hence are in an urgent need. Utilizing computational docking method and structure-based optimization strategy, we rationally designed and synthesized two series of isoxazol-3-yl- and isoxazol-5-yl-containing benzamide derivatives that targeted the bacterial cell division protein FtsZ. Evaluation of their activity against a panel of Gram-positive and -negative pathogens revealed that compounds B14 and B16 that possessed the isoxazol-5-yl group showed strong antibacterial activity against various testing strains, including methicillin-resistant Staphylococcus aureus and penicillin-resistant S. aureus. Further molecular biological studies and docking analyses proved that the compound functioned as an effective inhibitor to alter the dynamics of FtsZ self-polymerization via a stimulatory mechanism, which finally terminated the cell division and caused cell death. Taken together, these results could suggest a promising chemotype for development of new FtsZ-targeting bactericidal agent.

Substituted 1-(isoxazol-3-yl)methyl-1H-1,2,3-triazoles: Synthesis, palladium(II) complexes, and high-turnover catalysis in aqueous media

New substituted 3-((1H-1,2,3-triazol-1-yl)methyl)-5-arylisoxazoles (aryl = Ph, p-Tol) and 2-(5-phenylisoxazol-3-yl)-5-(2-(1-((5-(p-tolyl)isoxazol-3-yl)methyl)-1H-1,2,3-triazol-4-yl)ethyl)-1,3,4-oxadiazole were synthesized by means of click-chemistry proce

Design, synthesis and Structure-activity relationship studies of new thiazole-based free fatty acid receptor 1 agonists for the treatment of type 2 diabetes

The free fatty acid receptor 1 (FFA1/GPR40) has attracted interest as a novel target for the treatment of type 2 diabetes. Several series of FFA1 agonists including TAK-875, the most advanced compound terminated in phase III studies due to concerns about liver toxicity, have been hampered by relatively high molecular weight and lipophilicity. Aiming to develop potent FFA1 agonists with low risk of liver toxicity by decreasing the lipophilicity, the middle phenyl of TAK-875 was replaced by 11 polar five-membered heteroaromatics. Subsequently, systematic exploration of SAR and application of molecular modeling, leads to the identification of compound 44, which was an excellent FFA1 agonist with robustly hypoglycemic effect both in normal and type 2 diabetic mice, low risks of hypoglycemia and liver toxicity even at the twice molar dose of TAK-875. Meanwhile, two important findings were noted. First, the methyl group in our thiazole series occupied a small hydrophobic subpocket which had no interactions with TAK-875. Furthermore, the agonistic activity revealed a good correlation with the dihedral angle between thiazole core and the terminal benzene ring. These results promote the understanding of ligand-binding pocket and might help to design more promising FFA1 agonists.

Design, synthesis and biological evaluation of stilbene derivatives as novel inhibitors of protein tyrosine phosphatase 1B

By imitating the scaffold of lithocholic acid (LCA), a natural steroidal compound displaying Protein Tyrosine Phosphatase 1B (PTP1B) inhibitory activity, a series of stilbene derivatives containing phenyl-substituted isoxazoles were designed and synthesized. The structures of the title compounds were confirmed by 1H-NMR, 13C-NMR and HRMS. Activities of the title compounds were evaluated on PTP1B and the homologous enzyme TCPTP by using a colorimetric assay. Most of the target compounds had good activities against PTP1B. Among them, compound 29 (IC50 = 0.91 ± 0.33 μM), characterized by a 5-(2,3-dichlorophenyl) isoxazole moiety, exhibited an activity about 14-fold higher than the lead compound LCA and a 4.2-fold selectivity over TCPTP. Compound 29 was identified as a competitive inhibitor of PTP1B with a Ki value of 0.78 μM in enzyme kinetic studies.

Synthesis of functional isoxazole derivatives proceeding from (5-arylisoxazol-3-yl)chloromethanes

Reaction of 3-chloromethyl-5-phenyl(p-tolyl)isoxazoles with substituted phenols under the conditions of Williamson reaction afforded the corresponding 3-aryloxymethyl-5-phenyl(p-tolyl)isoxazoles. Treating the latter with sodium methylate, sodium phenyl(benzyl, furfuryl)thiolates and morpholine in methanol resulted in the replacement of the chlorine atom in 3-chloromethyl-5-phenyl(p-tolyl)isoxazoles by methoxy-, phenyl-(benzyl, furfuryl)sulfanyl groups and morpholine residue.

Rhodium-complex-catalyzed addition reactions of chloroacetyl chlorides to alkynes

(Chemical Equation Presented) The addition reaction of chloroacetyl chloride derivatives with terminal alkynes was found to be catalyzed by Rh(acac)(CO)(AsPh3) to afford (2)-1,4-dichloro-3-buten-2-one derivatives, which displayed diverse reactivities in s

Oxyiminoalkanoic acid derivatives with hypoglycemic and hypolipidemic activity

This invention provides a novel oxyiminoalkanoic acid derivative which has excellent hypoglycemic and hypolipidemic actions and which is used for the treatment of diabetes mellitus, hyperlipemia, insulin insensitivity, insulin resistance and impaired glucose tolerance.

Antibacterial monic acid derivatives

A compound of the formula (I) STR1 wherein R is a group STR2 R1 is hydrogen, phenyl, C1-20 alkyl, C2-8 alkenyl or C2-8 alkynyl each of which may optionally be substituted; or C3-7 cycloalkyl, X is a divalent group --Y--C=C--, and Y is oxygen or sulphur, have antibacterial and/or antimycoplasmal activity.