化学学报 ›› 2008, Vol. 66 ›› Issue (14): 1693-1699. 上一篇    下一篇

研究论文

四种5-氟尿嘧啶二肽衍生物的合成、晶体结构和抗癌活性

尹 萍 胡茂林* 严小威 王 舜
缪 谦 常雪琴 赵克俭   

  1. (温州大学化学与材料工程学院 温州 325027)
  • 投稿日期:2008-01-08 修回日期:2008-02-29 发布日期:2008-07-28
  • 通讯作者: 胡茂林

Synthesis, Crystal Structure and Anticarcinogenic Activity of Four 5-Fluorouracil-dipeptide Derivatives

YIN, Ping HU, Mao-Lin* YAN, Xiao-Wei WANG, Shun
MIAO, Qian CHANG, Xue-Qin ZHAO, Ke-Jian   

  1. (College of Chemistry and Materials Engineering, Wenzhou University, Wenzhou 325027)
  • Received:2008-01-08 Revised:2008-02-29 Published:2008-07-28
  • Contact: HU, Mao-Lin

合成了四种新的5-氟尿嘧啶(5-Fu)二肽衍生物, 它们的结构经过元素分析、IR、1H NMR和13C NMR的表征, 比旋光度[a]D的测定结果表明了它们之间的对映异构关系, 用X射线衍射法测定了其中一对对映异构的晶体结构3a (S)和3b (R), 生物活性测试的结果表明这四种化合物都具有一定的抑制活性, 并且R型产物比S型产物抑制率高. 研究了2a和3a与DNA在Au电极上相互作用的伏安行为, 比较了它们跟5-氟尿嘧啶与双链DNA发生相互作用的差别.

关键词: 5-氟尿嘧啶二肽衍生物, 晶体结构, 对映异构体, 抗癌活性, 循环伏安

Four new 5-fluorouracil-dipeptide derivatives were synthesized and identified by means of elemental analysis, IR, 1H NMR and 13C NMR spectra. The enantiomeric relations of the four isomers are reflected by their specific rotations [a]D data, two of which were determined by single crystal X-ray diffraction analysis. The result of the biological test shows that the four compounds have certain antitumor activities, and the R-isomer exhibites higher antibacterial activity than the S-isomer. The voltammetric behavior of 2a and 3a interacting with dsDNA on an Au electrode was investigated, and the interacting differences between them with 5-florouracil were compared.

Key words: 5-fluorouracil-dipeptide derivative, crystal structure, enantiomer, anticarcinogenic activity, cyclic voltammogram