17147-42-1

Usage

Chemical Properties

Colorless liquid

InChI:InChI=1/C8H11NO3/c1-4-11-8(10)7-5(2)9-12-6(7)3/h4H2,1-3H3

Upstream product

• 603-69-0 ethyl 2-acetylacetoacetate 
• 79-24-3 Nitroethane 
• 2723-42-4 ethyl 3-pyrrolidinobut-2-enoate 
• 74069-19-5 4-ethoxycarbonyl-3,5-dimethyl-5-nitro-2-isoxazoline 
• 141-97-9 ethyl acetoacetate 
• 70526-06-6 (Z)-3-pyrrolidin-1-yl-but-2-enoic acid ethyl ester 
• 52194-41-9 (Z)-ethyl 3-nitrobut-2-enoate 

Downstream Products

• 2510-36-3 3,5-dimethyl-4-isoxazolecarboxylic acid 
• 98484-97-0 3,5-dimethyl-1H-pyrazole-4-carboxylic acid hydrazide 
• 91901-20-1 3-methyl-5-styryl-isoxazole-4-carboxylic acid 
• 24380-47-0 3-methyl-5-styryl-isoxazole-4-carboxylic acid amide 
• 24380-41-4 3-methyl-5-styryl-isoxazole-4-carbonitrile 
• 97061-94-4 3-methyl-5-styryl-isoxazole-4-carbonyl chloride 
• 19788-36-4 4-hydroxymethyl-3,5-dimethylisoxazole 
• 159770-26-0 ethyl 5-bromomethyl-3-methyl-4-isoxazolecarboxylate 

Relevant academic research and scientific papers

Lipid accumulation inhibitory activities of novel isoxazole-based chenodeoxycholic acids: Design, synthesis and preliminary mechanism study

In continuation of our drug discovery program on hyperlipidemia, a series of novel isoxazole-chenodeoxycholic acid hybrids were designed, synthesized and evaluated for their lipid-lowering effects. Preliminary screening of all the synthesized compounds was done by using a 3T3-L1 adipocyte model, in which the most active compound 16b could significantly reduce the lipid accumulation up to 30.5% at a nontoxic concentration 10 μM. Further mechanism studies revealed that 16b blocked lipid accumulation via activating FXR-SHP signaling pathway, efficiently down-regulated the expression of key lipogenesis regulator SREBP-1c.

1,3-Dipolar cycloaddition route to nitrogen heterocyclic triones

1,3-Dipolar cycloaddition of nitrile oxides, formed in situ by dehydration of primary nitro compounds, with pyrrolidine enamines of protected γ- or δ-amino-β-keto esters affords isoxazole-4-carboxylates; these undergo lactam formation and N-O bond cleavage to afford 3-acyltetramic acids and 3-acyl-4-hydroxypyridin-2-ones.

Preparation of vinyl lactones and corresponding Mannich bases

Vinyl ketones and Mannich-bases obtained therefrom are useful as intermediates in the total synthesis of steroids having valuable pharmacological properties. These compounds are prepared by the low temperature reaction of a vinyl Grignard e.g., vinyl magnesium chloride with substituted γ, δ or ε lactones followed, if desired, by reaction of the vinyl ketone obtained with a primary or secondary amine. Particular compounds prepared by this procedure include 2-(2-substituted aminoethyl)-6-substituted-2-hydroxy-tetrahydropyrans and the tautomers thereof.