有机化学 ›› 2014, Vol. 34 ›› Issue (7): 1442-1446.DOI: 10.6023/cjoc201401035 上一篇    下一篇

研究简报

5-核糖或木糖亚甲基-2,4-咪唑啉二酮衍生物的合成及其杀菌活性

刘斌, 韩金涛, 汤博, 王明安   

  1. 中国农业大学应用化学系 北京 100193
  • 收稿日期:2014-01-21 修回日期:2014-03-05 出版日期:2014-07-25 发布日期:2014-04-15
  • 通讯作者: 王明安 E-mail:wangma@cau.edu.cn
  • 基金资助:

    “十二五”科技支撑计划(No.2011BAE06B03)资助项目.

Synthesis and Fungicidal Activity of D-Ribose and D-Xylose with Hydantion

Liu Bin, Han Jintao, Tang Bo, Wang Mingan   

  1. Department of Applied Chemistry, China Agricultural University, Beijing 100193
  • Received:2014-01-21 Revised:2014-03-05 Online:2014-07-25 Published:2014-04-15
  • Supported by:

    Project supported by the National Key Technologies R&D Program (No. 2011BAE06B03).

以1,2:5,6-O-二异丙叉-α-D-呋喃葡萄糖为原料,经过吡啶重铬酸盐(PDC)氧化、NaBH4还原及选择性水解,实现α-D-木糖环向α-D-核糖环的C(3)位羟基构型的转化,然后分别在高碘酸钠氧化作用下得到糖环上C(5)位为醛基的α-D-木糖和α-D-核糖衍生物,它们分别与2,4-咪唑啉二酮-5-膦酸酯及2-硫代-2,4-咪唑啉二酮发生Wittig-Horner反应及Knoevenagel反应,分离得到3对5-核糖或木糖亚甲基-2,4-咪唑啉二酮衍生物顺反异构体,它们的化学结构经1H NMR,IR,MS和X射线单晶衍射确证. 初步生物活性测定结果表明: 在50 μg/mL浓度下,部分目标化合物均对供试菌种显现出一定的抑制活性.

关键词: 2,4-咪唑啉二酮, 木糖, 核糖, 杀菌活性

The α-D-ribose and α-D-xylose C(5)-aldehyde derivatives (1 and 2) were prepared through four and two steps using 1,2:5,6-di-O-isopropylidene-α-D-glucofuranose as raw material. Then 1 and 2 reacted with hydantoin phosphonate and 2-thiohydantoin by Wittig-Horner and Knoevenagel reaction to afford 3 pairs of E and Z isomers of target products 35. Their structures were elucidated by 1H NMR, 13C NMR, IR, MS and X-ray diffraction. The preliminary bioassay results showed that some of them have certain fungicidal activities against 7 plant pathogens at the concentration of 50 μg/mL.

Key words: hydantoin, ribose, xylose, fungicidal activity