61448-99-5

Upstream product

• 300-87-8 3,5-dimethyl-1,2-oxazole 
• 100-52-7 benzaldehyde 
• 27349-51-5 (3-methyl-5-isoxazolyl)methyl phenyl ketone 
• 100-47-0 benzonitrile 
• 123-54-6 acetylacetone 
• 62759-26-6 ((3-methylisoxazol-5-yl)methyl)lithium 

Downstream Products

• 61449-25-0 5-Amino-1-hydroxy-1-phenyl-hexen-4-on-⁽³⁾ 
• 51101-01-0 3-methyl-5-styryl-isoxazole 
• 108401-87-2 5-hydroxy-1,7-diphenylhepta-1,4,6-trien-3-one 

Relevant academic research and scientific papers

Asymmetric transfer hydrogenation of heterocycle-containing acetophenone derivatives using N-functionalised [(benzene)Ru(II)(TsDPEN)] complexes

The application of enantiomerically-pure ruthenium(II) catalysts containing N - functionalised TsDPEN ligand to the asymmetric transfer hydrogenation of 15 examples of α-heterocyclic acetophenone derivatives is reported. Products of up to 99% ee were formed.

Reductive ring opening of 3,5-bis(2-arylethenyl)isoxazoles with molybdenum hexacarbonyl: A novel route to symmetrical and unsymmetrical curcumin derivatives

Curcumin derivatives were successfully synthesized from 3,5-dimethylisoxazole by lateral metalation and condensation with various aromatic aldehydes sequentially at C5- and C3-methyl groups. After dehydration, further transformation of isoxazole ring to β-diketone moiety was accomplished by reductive ring opening using molybdenum hexacarbonyl [Mo(CO)6] and subsequent simple acidic hydrolysis.

Structure-activity relationship and improved hydrolytic stability of pyrazole derivatives that are allosteric inhibitors of West Nile Virus NS2B-NS3 proteinase

West Nile Virus (WNV) is a potentially deadly mosquito-borne flavivirus which has spread rapidly throughout the world. Currently there is no effective vaccine against flaviviral infections. We previously reported the identification of pyrazole ester derivatives as allosteric inhibitors of WNV NS2B-NS3 proteinase. These compounds degrade rapidly in pH 8 buffer with a half life of 1-2 h. We now report the design, synthesis and in vitro evaluation of pyrazole derivatives that are inhibitors of WNV NS2B-NS3 proteinase with greatly improved stability in the assay medium.

Synthesis of optically active β'-hydroxy-β-enaminoketones via enzymatic resolution of carbinols derived from 3,5-disubstituted isoxazoles

The preparation of several enantiomerically pure β'-hydroxy-β-enaminoketones from the corresponding isoxazolic carbinols, which have been obtained by enzymatic kinetic resolution of the racemic β-hydroxyisoxazoles catalyzed by lipases, is described. The enzymatic transesterification of racemic (±)-5-(2-hydroxypropyl)-3-methylisoxazole 3a, and racemic (±)-5-(2-hydroxy-2-p-tolylethyl)-3-methylisoxazole 3d, has been studied with respect to the influence of experimental variables such as the used enzyme, the acylating agent or the solvent on the enantioselectivity of the reaction. After the reductive cleavage of the isoxazolic ring of the enantiopure carbinols, (R)- and (S)-2-amino-4-oxo-2-hepten-6-ol, (R)- and (S)-5, and (R)-2-amino-6-p-tolyl-4-oxo-2-hexen-6-ol, (R)-7 with an enantiomeric excess >98% were obtained. Copyright (C) 2000 Elsevier Science Ltd.

Lewis acid mediated addition of tri-n-butyl-stannylmethylisoxazole with aldehydes

Lewis acid mediated addition of 5-(tri-n-butylstannyl)methyl-3-methylisoxazole and its analogues with aldehydes have been carried out. Corresponding 5-(β-hydroxy)ethylisoxazoles were obtained in moderate yields, without ring opening of the isoxazole.

Styrylpyrazoles, styrylisoxazoles, and styrylisothiazoles. Novel 5-lipoxygenase and cyclooxygenase inhibitors

A series of styrylpyrazoles, styrylisoxazoles, and styrylisothiazoles were prepared and found to be dual inhibitors of 5-lipoxygenase and cyclooxygenase in rat basophilic leukemia cells. Compounds from this series also were found to inhibit the in vivo production of LTB4 when dosed orally in rats. Among these compounds, di-tert-butylphenols 19 and 33 exhibit oral activity in various models of inflammation and, most importantly, are devoid of ulcerogenic potential.

ISOXAZOLES AS 4b-DIKETONE SYNTHONS-SELECTIVE ANION FORMATION ON 3,5-DIALKYLISOXAZOLES

3,5-Dimethylisoxazole can be metalated and alkylated regiospecifically.Alkylation occurs first on the 5-methyl group, and a second alkylation occurs on the 3-methyl group.This method permits specific synthesis of disubstituted isoxazoles, and of the corresponding β-diketones.