Chin. J. Org. Chem. ›› 2010, Vol. 30 ›› Issue (01): 92-97. Previous Articles     Next Articles

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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

王宝雷,马瑞典,李永红,宋海滨,李正名*   

  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)
  • 收稿日期:2009-04-30 修回日期:2009-07-14 发布日期:2010-01-20
  • 通讯作者: 李正名 E-mail:nkzml@vip.163.com
  • 基金资助:

    国家重点基础研究发展计划项目(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)

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

Wang,Baolei,Ma,Ruidian,Li,Yonghong,Song,Haibin,Li,Zhengming*   

  1. (State-Key Laboratory of Elemento-Organic Chemistry,Elemento-Organic Chemistry Institute, Nankai University,Tianjin 300071)
  • Received:2009-04-30 Revised:2009-07-14 Published:2010-01-20

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.

Key words: oxadiazole, synthesis, crystal structure, biological activity