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3,4-二-O-甲基-D-甘露醇的合成及其抗肿瘤活性的研究

Synthesis and antibacterial activities of 3,4-di-O-methyl-D-mannitol

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【作者】 詹天荣郑立陈海敏宋金明

【Author】 ZHANG Tian-rong~(1,2,3),ZHENG Li~(1,2),CHEN Hai-min~(1,2),SONG Jin-ming~1 (1.Institute of Oceanology,Chinese Academy of Sciences,Qingdao266071;Graduate School of Chinese Academy of Sciences, Beijing100039,China;2.Institute of Oceanology,Chinese Academy of Sciences,Qingdao26607,China 3.School of Pharmaceatical Sciences,Shandong vniversity,Jinan250012,China)

【机构】 中国科学院海洋研究所中国科学院海洋研究所 山东青岛 266071中国科学院研究生院北京 100039山东大学药学院山东济南 250012山东青岛 266071中国科学院研究生院北京 100039山东青岛 266071

【摘要】 以D 甘露醇为原料,先与丙酮缩合合成1,2,5,6 二 O 异亚丙基 D 甘露醇,再对剩下的3,4位上的羟基进行甲醚化,同时脱去异亚丙基保护基团,经两步反应合成了目标化合物3,4 二 O 甲基 D 甘露醇,产率约60%。抗肿瘤活性表明IC50(宫颈癌细胞样)为4 5μg/mL,IC50(口腔表皮样癌细胞样)为10μg/mL。

【Abstract】 D-mannitol extracted from seaweed was used as crude materials,after being acetalated with acetone,hydroxyls of C-1,C-2,C-5 and C-6 were protected.Then hydroxyls of C-3 and C-4 were respectively etherealized with methyl iodide.Finally,isopropylidenes were deprotected and hydroxyls of C-1,C-2,C-5 and C-6 were returned.After two steps reaction,title compound,3,4-di-O-methyl-D-mannitol was prepared.Its total productivity is 43.32~50.92% and its melting point is 148~150℃.By analyzing datum from IR,Element analysis,()1H-NMR,()13C-NMR and ESI-MS,structures of intermedium and title compound were confirmed to be same as their molecular formulas.In addition,the vitro antitumor effects of title compound were investigated,which showed that the inhibition rates on the tumor cells were directly proportional to its concentrations.However,at the same concentration,the antitumor effects of 3,4-di-O-methyl-D-mannitol on tumor cells KB and Hela were obviously better than that on cell HL-7702,and there existed some proportional relationship between effects and dosages.

【关键词】 D-甘露醇酯合成抗肿瘤
【Key words】 D-mannitolsynthesisantitumor effect
【基金】 中国科学院方向性创新项目(KZCX3 SW 215);国家杰出青年科学基金资助项目(49925614)
  • 【文献出处】 化学研究与应用 ,Chemical Research and Application , 编辑部邮箱 ,2004年06期
  • 【分类号】O621;R730.4
  • 【被引频次】3
  • 【下载频次】136
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