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有机化学
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有机化学 ›› 2004, Vol. 24 ›› Issue (12): 1601-1605. 上一篇    下一篇

研究简报

N-茄呢基胺类糖酯化合物的合成及生理活性

赵瑾a, 刘蕾a, 宋金勇a,b, 王超杰*,a   

  1. a河南大学化学化工学院 开封 475001
    b许昌卷烟总厂技术中心 许昌 461000
  • 收稿日期:2004-03-01 修回日期:2004-06-12 接受日期:2004-06-12 发布日期:2022-09-20
  • 基金资助:
    国家自然科学基金(No. 20272039)和教育部留学回国人员基金资助项目

Synthesis and Biological Activity ofGlycosyl N-Solanesylaminocarboxylic Esters

ZHAO Jina, LIU Leia, SONG Jin-Yonga,b, WANG Chao-Jie*,a   

  1. aCollege of Chemistry and Chemical Engineering, Henan University, Kaifeng 475001
    bThe Technological Centre, Xuchang Cigarette Factory, Xuchang 461000
  • Received:2004-03-01 Revised:2004-06-12 Accepted:2004-06-12 Published:2022-09-20
  • Contact: *E-mail: schemorg@mail.sc.cninfo.net

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在氢氧化钠和四丁基溴化铵存在下,将化合物2-N-茄呢基胺基苯甲酸(3)和N-茄呢基己二酰胺酸(6)分别与O-乙酰基溴代葡萄糖、O-乙酰基溴代半乳糖、O-乙酰基溴代乳糖和O-乙酰基溴代麦芽糖反应制得对应的糖酯4a～4d和7a～7d,由元素分析,IR, 1H NMR和MS确证了8个新化合物的结构,并对其中6个化合物(4a, 4d 和7a～7d)在三种癌细胞模型上进行了一些初步体外生理活性的测试.

关键词: 2-N-茄呢基胺基苯甲酸, N-茄呢基己二酰胺酸, 糖酯, 合成, 生理活性

Four glycosyl 2-(N-solanesylamino) benzoates (4a～4d) and four glycosyl 5-(N-solanesylamino~carbonyl)pentanoates (7a～7d) were first designed and synthesized respectively by the reaction of 2-N-solanesylamino-benzoic acid (3) or 5-(N-solanesylaminocarbonyl)pentanoic acid (6) with O-acetylglucopyranosyl bromide, O-acetylgalactopyranosyl bromide, O-acetyllactosyl bromide and O-acetylmaltobiosyl bromide in the presence of Bu4NBr. Their structures were confirmed by IR, 1H NMR, MS spectra and elemental analysis. Six compounds (4a, 4d and 7a～7d) werestudied preliminarily for their anti-tumor activity in vitro on KB, Bel-7402 and HCT-8 cells.

Key words: 2-N-solanesylamino-benzoic acid, 5-(N-solanesylaminocarboxyl)pentanoic acid, glucosyl ester, synthesis, bioactivity