Synthesis and Antiviral Activities of Pyrazole Derivatives Containing an Oxime Moiety

被引：221

作者：

Ouyang, Guiping ^{[1
]}

Cai, Xue-Jian ^{[1
]}

Chen, Zhuo ^{[1
]}

Song, Bao-An ^{[1
]}

Bhadury, Pinaki S. ^{[1
]}

Yang, Song ^{[1
]}

Jin, Lin-Hong ^{[1
]}

Xue, Wei ^{[1
]}

Hu, De-Yu ^{[1
]}

Zeng, Song ^{[1
]}

机构：

[1] Guizhou Univ, Minist Educ, Key Lab Green Pesticide & Agr Bioengn, Ctr Res & Dev Fine Chem, Guiyang 550025, Peoples R China

来源：

JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY | 2008年 / 56卷 / 21期

基金：

中国国家自然科学基金;

关键词：

Pyrazole; oxime ethers moiety; antiviral activity; synthesis;

D O I：

10.1021/jf802489e

中图分类号：

S [农业科学];

学科分类号：

09 ;

摘要：

Target compounds 4a-n were obtained by the reaction of 1-substituted phenyl-3-methyl-5-substituted phenylthio-4-pyrazolaidoximes (3) with chloromethylated heterocyclic compounds (CICH2-R-3) under reflux conditions in ethanol. Subsequently, the oxidation of 4a-e with KMnO4 in HOAc at room temperature afforded eight new compounds, 5a-h. The synthesized compounds were characterized by physical constants, and the structures of the title compounds were confirmed by IR, H-1 NMR, C-13 NMR, and elemental analysis. The bioassay revealed that the compounds possessed antiviral activities. It was found that title compounds 4a and 4g had the same inactivation effects against TMV (EC50 = 58.7 and 65.3 mu g/mL) as the commercial product Ningnanmycin (EC50 = 52.7 mu g/mL). To the best of our knowledge, this is the first report on the antiviral activity of pyrazole derivatives containing an oxime moiety.

引用

页码：10160 / 10167

页数：8

共 24 条

[1] Synthesis and fungicidal activity against Rhizoctonia solani of 2-alkyl (alkylthio)-5-pyrazolyl-1,3,4-oxadiazoles (thiadiazoles) [J].