132319-05-2

Upstream product

• 188883-54-7 2-benzoyl-3-(4-hydroxy-phenyl)-acrylic acid ethyl ester 
• 94-02-0 ethyl 3-oxo-3-phenylpropionate 
• 123-08-0 4-hydroxy-benzaldehyde 
• 1076-59-1 3-phenyl-4H-isoxazol-5-one 
• 7713-79-3 3-phenyl-5-isoxazolone 
• 127916-11-4 ethyl bezoylacetate oxime 

Relevant academic research and scientific papers

Facile and expedient synthesis of α,β-unsaturated isoxazol-5(4H)-ones under mild conditions

Abstract: It was found that nano-SiO2–H2SO4 was catalyzed by the three-component cyclocondensation of aryl/heteroaryl aldehydes, hydroxylamine hydrochloride, and β-ketoesters toward the synthesis of α,β-unsaturated?isoxazol-5(4H)-ones under green conditions. The reaction yielded the corresponding heterocycles at room temperature in relatively shorter reaction times. It merits mentioning that the mild conditions allow the synthesis of several α,β-unsaturated?isoxazol-5(4H)-ones using this method. In this study, some new derivatives of isoxazolones were also synthesized and characterized. It is efficient, clean, simple, safe, and ecologically friendly. This straightforward method is cost-effective and requires no preparation of reactants. The three-component annulation was performed without using energy sources, for example, heat, ultrasound wave, and microwave irradiation. Graphic abstract: [Figure not available: see fulltext.].

The tyrosinase inhibitory effects of isoxazolone derivatives with a (Z)-β-phenyl-α, β-unsaturated carbonyl scaffold

Thirteen (Z)-4-(substituted benzylidene)-3-phenylisoxazol-5(4H)-ones were designed to confirm the geometric effect of the double bond of the β-phenyl-α, β-unsaturated carbonyl scaffold on tyrosinase inhibitory activity. Compounds 1a–1m, which all possessed the (Z)-β-phenyl-α, β-unsaturated carbonyl scaffold, were synthesized using a tandem reaction consisting of an isoxazolone ring formation and a Knoevenagel condensation, and three starting materials, ethyl benzoylacetate, hydroxylamine and benzaldehydes. Some of the compounds showed inhibitory activity against mushroom tyrosinase as potent as compounds containing the “(E)”-β-phenyl-α, β-unsaturated carbonyl scaffold. Compounds 1c and 1m showed greater inhibitory activity than kojic acid: IC50 = 32.08 ± 2.25 μM for 1c; IC50 = 14.62 ± 1.38 μM for 1m; and IC50 = 37.86 ± 2.21 μM for kojic acid. A kinetic study indicated that 1m inhibited tyrosinase in a competitive manner and that it probably binds to the enzyme's active site. In silico docking simulation supported binding of 1m (?7.6 kcal/mol) to the active site of tyrosinase with stronger affinity than kojic acid (?5.7 kcal/mol). Similar results were obtained using cell-based assays, and in B16F10 cells, compound 1m dose-dependently inhibited tyrosinase activity and melanogenesis. These results indicate the anti-melanogenic effect of compound 1m is due to the inhibition of tyrosinase and (Z)-isomer of the β-phenyl-α, β-unsaturated carbonyl scaffold can, like its congener the (E)-isomer, act as an excellent scaffold for tyrosinase inhibition.

Fast and efficient synthesis of 4-arylidene-3-phenylisoxazol-5-ones

A convenient and easy synthesis of 4-arylidene-3-phenylisoxazol-5-ones by the three-component reaction of hydroxylamine, ethyl benzoylacetate and aromatic aldehydes in the presence of DABCO in refluxing ethanol is reported.