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有机化学.pdfVIP

DOI: 10.6023/cjoc201401035 研究简报 有机化学 Chinese Journal of Organic Chemistry NOTE 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* ( 中国农业大学应用化学系 北京 100193) 摘要 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 Synthesis and Fungicidal Activity of D-Ribose and D-Xylose with Hydantion Liu, Bin Han, Jintao Tang, Bo Wang, Mingan* (Department of Applied Chemistry, China Agricultural University, Beijing 100193) Abstract 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 3～5. 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. Keywords hydantoin; ribose; xylose; fungicidal activity 在天然产物中经常发现单