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

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%.

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

A series of novel 1,3,4-oxadiazole title compounds were synthesized by the Huisgen reaction from 2-(4-(1H-tetrazol-5-y1)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,~(13)C 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.