Stereoselective synthesis and antifungal activities of (E)-α-(methoxyimino)benzeneacetate derivatives containing 1,3,5-substituted pyrazole ring
Stereoselective synthesis and antifungal activities of (E)-α-(methoxyimino)benzeneacetate derivatives containing 1,3,5-substituted pyrazole ring
复制标题
DOI：
10.1021/jf060074f
复制
发表时间：
2006-05-17
影响因子：
6.1
通讯作者：
Liu, Zhao-Jie
中科院分区：
文献类型：
--
作者：
Li, Yan;Zhang, Hong-Quan;Liu, Zhao-Jie
立体选择性地合成了13个新的（E）- R-（甲氧亚氨基）苯乙酸酯衍生物，它们是嗜球果伞素的类似物，含有（E）-甲氧亚氨基乙酸甲酯和1，3，5-取代吡唑环两个药效子结构。发现偶联反应可以立体选择性地得到（E：Z ca. 14：1）关键中间体（E）-2-（羟基亚氨基）2-邻甲苯基乙酸甲酯（2）。在代表性产品中进行X射线晶体结构测定。初步生物活性测定结果表明，化合物1对水稻纹枯病菌、灰霉病菌、玉米赤霉菌、梨轮纹病菌和梨小斑病菌均表现出较强的杀菌活性。
Thirteen novel ( E)- R-( methoxyimino) benzeneacetate derivatives, the analogues of strobilurins, which contain two pharmacophoric substructures of the methyl ( E)- methoxyiminoacetate moiety and 1,3,5-substituted pyrazole ring, were stereoselectively synthesized. It was found that the coupling reaction could give stereoselectively ( E: Z ca. 14: 1) the key intermediate material ( E)- methyl 2-( hydroxyimino)2- o- tolyl acetate ( 2). An X- ray crystallographic structure determination was carried out in a representative product. The preliminary bioassays indicated that all of the compounds 1 showed potent fungicidal activity against Rhizoctonia solani, Botrytis cinereapers, Gibberella zeae, Physalospora piricola, and Bipolaris mayclis.