• Bulletin of the Korean Chemical Society
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• v.33 no.6
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• pp.1979-1982
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• 2012

Oxime ethers of ${\beta}$-oxo-${\gamma}$-phenylbutanoic acids were prepared to develop more effective PPAR ${\alpha}$ and ${\gamma}$ dual agonists. Among them, compound 11k exhibited potent $in$ $vitro$ activities with $EC_{50}$ of 2.5 nM and 3.3 nM in PPAR ${\alpha}$ and ${\gamma}$, respectively. It showed better glucose lowering effects than rosiglitazone 1 and improved the lipid profile like plasma triglyceride in db/db mice model.

• The Korean Journal of Pesticide Science
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• v.8 no.4
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• pp.258-264
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• 2004

The pyrazole family was discovered as effective insecticides/acaricides, and fenpyroximate and tebufenpyrad were introduced in the market. In this study, new series of pyrazole oxime ethers were designed and synthesized. The pyrazolone 1 was prepared by the condensation of ethyl acetoacetate with methylhydrazine, and then subsequently subjected to the Vilsmeier-Haack chloroformylation yielding 4-formyl-5-chloro-pyrazole 2. The nucleophilic aromatic substitution of 2 generally allowed the introduction of a wide range of heterocycles into the pyrazole ring. The resulting pyrazole aldehydes 3a-i were readily converted to the corresponding pyrazole oxime derivatives 4a-i, and subsequently to 5-substituted pyrazole oxime ether derivatives 6a-i. The screening assay results clearly show that the activities of 6d were comparable to those of fenpyroximate (6a) against BPH, DBM, and TSSM. It indicates that 6d has a potential to be developed as an insecticidal agent.

• Bulletin of the Korean Chemical Society
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• v.15 no.1
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• pp.53-57
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• 1994

A comparison study on asymmetric borane reduction of ketoxime ethers and N-substituted ketimines possesing C = N double bond mediated by the selected chiral oxazaborolidines (1-6) was investigated. Thus, an aromatic ketoxime O-alkyl ether acetophenone oxime O-methyl ether was reduced to the corresponding amine (1-phenylethylamine 8a) with optical yields, such as 58% ee with 1, 86% ee with 2, 3% ee with 3, 99% ee with 4, 60% ee with 5, and 73% ee with 6. However, the reduction of an aliphatic ketoxime derivative 2-heptanone oxime O-methyl ether provided low optical inductions (7-13% ee). For ketoxime O-trimethylsilyl ethers, the reduction of acetophenone O-trimethylsilyl ether afforded 8a with optical yields which were 90% ee with 1, 40% ee with 2, 2% ee with 3, 62% ee with 4, 5% ee with 5, and 60% ee with 6. The reduction of 2-heptanone O-trimethylsilyl ether also gave the product amine with low optical yields (10-40% ee). In the case of N-substituted ketimines, the reduction of acetophenone N-phenylimine afforded the corresponding amine with 79% ee, 78% ee, 9% ee, 73% ee, 78% ee and 67% ee using 1, 2, 3, 4, 5, and 6, respectively, whereas low optical inductions (5-18% ee) for 2-heptanone N-phenylimine were achieved.