有机化学 ›› 2012, Vol. 32 ›› Issue (05): 943-948.DOI: 10.6023/cjoc1111291 上一篇    下一篇

研究简报

噻唑烷-4-酮连假三糖的合成及其对T 淋巴细胞增殖活性研究

陈华a, 高芳a, 殷庆梅a, 李春晓b, 李娜b, 孟明b, 李小六a   

  1. a 河北大学化学与环境科学学院 保定 071002;
    b 河北大学医学部 河北省化学生物学重点实验室 保定 071002
  • 收稿日期:2011-11-29 修回日期:2011-12-12 发布日期:2012-01-06
  • 通讯作者: 李小六 E-mail:lixl@hbu.cn
  • 基金资助:

    国家自然科学基金(Nos. 20972039, 21172051)、河北省自然科学基金(No. B2011201169)、河北省教育厅自然科学基金(Nos. 2009309, ZH2011110,Y2011119)、河北省科学技术研究与发展计划(No. 09276418D-13)资助项目.

Synthesis and Proliferative Effects on T Lymphocytes of Novel Thiazolidin-4-one Linked Pseudotrisaccharides

Chen Huaa, Gao Fanga, Yin Qingmeia, Li Chunxiaob, Li Nab, Meng Mingb, Li Xiaoliua   

  1. a Key Laboratory of Chemical Biology of Hebei Province, College of Chemistry and Environmental Science,Hebei University, Baoding 071002;
    b Medical School, Hebei University, Baoding 071002
  • Received:2011-11-29 Revised:2011-12-12 Published:2012-01-06
  • Supported by:

    Project supported by the National Natural Science Foundation of China (Nos. 20972039, 21172051), the Natural Science Foundation of Hebei Province (No. B2011201169), the Natural Science Foundations of Education Department of Hebei Province (Nos. 2009309, ZH2011110, Y2011119), and the Program of Science and Technology of Hebei Province (No. 09276418D-13).

以双叠氮基糖1、糖醛2 和巯基乙酸为原料, 室温条件下, 利用Staudinger/aza-Wittig/环合一锅法反应, 合成了新型噻唑烷-4-酮连假三糖衍生物3a 和3b, 并经脱苯甲酰基(Bz)保护基, 分别得到了相应产物4a 和4b. 初步生物活性测试表明, 化合物4a 和4b 能显著促进T 淋巴细胞增殖, 具有较强的免疫增强活性.

关键词: 噻唑烷-4-酮, 假三糖, 免疫增强剂

Novel thiazolidin-4-one-linked pseudotrisaccharides 3a and 3b were synthesized by the one-pot tandem Staudinger/ aza-Wittig/cyclization reaction at room temperature starting from a bis-azidosugar, a sugar aldehyde and mercaptoacetic acid. The debenzoylation of 3a and 3b afforded the corresponding compounds 4a and 4b, respectively. The preliminary biological evaluation of compounds 4a and 4b showed that compounds 4a and 4b had significant effects on T-cell proliferation, and hold potential as immunostimulating agents.

Key words: thiazolidin-4-one, pseudotrisaccharides, immunostimulating agent