123862-91-9

Upstream product

• 16883-16-2 5-methyl-3-phenylisoxazole-4-carbonyl chloride 
• 62-53-3 aniline 
• 1136-45-4 5-methyl-3-phenylisoxazol-4-carboxylic acid 
• 100-52-7 benzaldehyde 
• 102-01-2 N-phenylacetoacetamide 
• 698-16-8 benzohydroximoyl chloride 

Downstream Products

• 408528-01-8 5-methyl-3,N-diphenyl-isoxazole-4-carboximidoyl chloride 
• 87967-95-1 5-methyl-3-phenylisoxazole-4-carboxaldehyde 
• 1136-45-4 5-methyl-3-phenylisoxazol-4-carboxylic acid 
• 93-91-4 1-phenylbutan-1,3-dione 

Relevant academic research and scientific papers

Synthesis of 3,4,5-trisubstituted isoxazoles in water via a [3 + 2]-cycloaddition of nitrile oxides and 1,3-diketones, β-ketoesters, or β-ketoamides

Herein we report a method for the synthesis of 3,4,5-trisubstituted isoxazoles in water under mild basic conditions at room temperature via a [3 + 2]-cycloaddition of nitrile oxides and 1,3-diketones, β-ketoesters, or β-ketoamides. We optimized the reaction conditions to control the selectivity of the production of isoxazoles and circumvent other competing reactions, such as O-imidoylation or hetero [3 + 2]-cycloaddition. The reaction happens fast in water and completes within 1-2 hours, which provides an environmentally friendly access to 3,4,5-trisubstituted isoxazoles, an important class of structures found in numerous bioactive natural products and pharmaceuticals. Additionally, we optimized the reaction conditions to produce trifluoromethyl-substituted isoxazoles, a prevalent scaffold in biomedical research and drug discovery programs. We also proposed a plausible mechanism for the selectivity of the [3 + 2]-cycloaddition reaction to produce 3,4,5-trisubstituted isoxazoles. Not to be overlooked are our optimized reaction conditions for the dimerization of hydroximoyl chlorides to form furoxans also known as 1,2,5-oxadiazole 2-oxides, a class of structures with important biological activities due to their unique electronic nature and coordination ability.

Design, synthesis, and biological evaluation of phenyl-isoxazole-carboxamide derivatives as anticancer agents

The present study aimed to design and synthesize a series of phenyl-isoxazole-carboxamide derivatives and investigate their antitumor and antioxidant activities. The in vitro cytotoxic evaluation was conducted using the MTS assay against four cancer cell lines: hepatocellular carcinoma (Hep3B and HepG2), cervical adenocarcinoma (HeLa), breast carcinoma (MCF-7), in addition to the normal cell line (Hek293T). Besides, the antioxidant activity was evaluated using a 2,2-diphenyl-1-picrylhydrazyl (DPPH) assay. All obtained compounds were found to have potent to moderate activities against Hep3B and MCF-7 cancer cells lines, except compound 2e. It was found that compound 2a has potent activity against HeLa and Hep3B cancer cell lines with IC50 values of 0.91 and 8.02 μM, respectively. The IC50 dose range of the tested compounds against Hep3B was 5.96-28.62 μM, except for 2e, compared with doxorubicin, which has an IC50 value of 2.23 μM. Also, the IC50 value range of the compounds against Hek293T was 112.78-266.66 μM, compared with doxorubicin, which has an IC50 dose of 0.581 μM. The antioxidant activity of the synthesized compounds was weak, and compound 2d showed moderate activity against the DPPH enzyme with an IC50 value of 138.50 μM in comparison with Trolox, which has an IC50 dose of 37.23 μM.

Enolate-mediated 1,3-dipolar cycloaddition reaction of β-functionalized ketones with nitrile oxides: Direct access to 3,4,5-trisubstituted isoxazoles

TMG-catalyzed [3 + 2] organocatalytic 1,3-dipolar cycloaddition reactions of β-functionalized ketones with nitrile oxides have been developed. This strategy could generate 3,4,5-trisubstituted isoxazoles in high yields and regioselectivities.

Synthesis method of 3,4,5-trisubstituted isoxazole type compound

The invention discloses a synthesis method of a 3,4,5-trisubstituted isoxazole type compound. In reaction solvent, the 3,4,5-trisubstituted isoxazole type compound is obtained through reaction with substituted acetoacetamide and chloro-substituted aldoxim

Straightforward transformation of isoxazoles into pyrazoles: renewed and improved

Isoxazoles bearing alkyl or carbamoyl groups were transformed into the corresponding pyrazoles in high yields by the treatment with hydrazine in methanol in the presence of a hydrogenation catalyst, e.g., Raney nickel, at ambient temperature. For the synthesis of N-substituted pyrazoles, hydrogenolysis of isoxazole followed by the treatment with substituted hydrazine was required. 3(5)-Aryl- or acylamido-substituted isoxazoles are less suitable for such transformations.