2-[4-(5-取代-1,3,4-噁二唑-2-基)苯氧基]丙酸/乙酸酯的合成、结构及其生物活性  

Synthesis,Structure and Biological Activity of 2-[4-(5-Substituted-1,3,4-oxadiazol-2-yl)phenoxy] Propanoate/Acetate

作　　者：王宝雷[1] 马瑞典[1] 李永红[1] 宋海滨[1] 李正名[1] 

机构地区：[1]南开大学元素有机化学研究所元素有机化学国家重点实验室,天津300071

出　　处：《有机化学》2010年第1期92-97,共6页Chinese Journal of Organic Chemistry

基　　金：国家重点基础研究发展计划(No.2003CB114406);高等学校博士学科点专项科研基金(No.20070055044);天津市应用基础及前沿技术研究计划(No.08JCYBJC00800)资助项目

摘　　要：以4-氰基苯酚和2-氯丙酸乙酯(或2-氯乙酸甲酯)为起始原料进行反应,得到2-(4-(1H-四唑-5-基)苯氧基)丙酸/乙酸酯,进而发生Huisgen反应合成了一系列新型1,3,4-噁二唑类标题化合物,其结构经~1H NMR,^(13)C NMR,IR,MS及元素分析或高分辨质谱得到表征和确认.用X射线衍射测定了化合物3q的晶体结构.初步生物活性测试结果表明,含有较小体积取代基的噁二唑化合物3c和3d在200μg/mL测试浓度下对水稻KARI酶分别具有94.5%和83.1%的抑制活性.化合物3p在100μg/mL浓度下对双子叶油菜(Brassica campestris)胚根生长抑制率可达82.4%.A series of novel 1,3,4-oxadiazole title compounds were synthesized by the Huisgen reaction from 2-（4-（1H-tetrazol-5-yl）phenoxy）propanoate/acetate. The latter was obtained via 4-cyanophenol and ethyl 2-chloropropanoate （or methyl 2-chloroacetate） as starting materials. Structures of the title compounds were confirmed by 1H NMR, 13C NMR, MS, IR techniques and elemental analysis or FT-MS, and the structure of 3q was determined by X-ray single crystal diffraction method. The preliminary bioassay indicates that compounds 3c and 3d with small volume substituents on the oxadiazole ring showed 94.5% and 83.1% inhibitory activities on rice KARI at a test concentration of 200 μg/mL, repectively. Compound 3p displayed 82.4% inhibition on rape root （Brassica campestris） at 100 μg/mL concentration in herbicidal tests.

关 键 词：噁二唑 合成 晶体结构 生物活性 

分 类 号：TQ450.1[化学工程—农药化工]