高等学校化学学报

高等学校化学学报

• 研究论文 • 上一篇    下一篇

2-氨基-5-烷基-1,3,4-噻二唑修饰环糊精的制备与表征

孙乐, 范晓东, 刘郁杨   

  1. 西北工业大学理学院应用化学系, 西安 710072
  • 收稿日期:2005-10-09 修回日期:1900-01-01 出版日期:2006-09-10 发布日期:2006-09-10
  • 通讯作者: 范晓东

Preparation and Characterization of β-Cyclodextrin Modified by 5-Alkyl-2-amino-1,3,4-thiadiazoles

SUN Le, FAN Xiao-Dong, LIU Yu-Yang   

  1. Department of Applied Chemistry, School of Science, Northwestern Polytechnical University, Xi'an 710072, China

  • Received:2005-10-09 Revised:1900-01-01 Online:2006-09-10 Published:2006-09-10
  • Contact: FAN Xiao-Dong

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被引次数

8

摘要： 在N2气保护下, 用单-(6-对甲苯磺酰基)-CD(β-CD-6-OTs)和过量的2-氨基-5-烷基-1,3,4-噻二唑在80 ℃反应2 d, 合成了5种新的2-氨基-5-烷基-1,3,4-噻二唑修饰β-环糊精. 化合物的结构用IR, 1H NMR, 13C NMR, UV, MS和元素分析等方法进行了表征. 由于环糊精的屏蔽效应, 在2-氨基-1,3,4-噻二唑修饰β-环糊精的 1H NMR中, 修饰产物中的噻二唑质子发生了高场位移. 其它的谱图数据同理论值相吻合, 这证明合成与分离方法是可行的. 研究了产物的生物活性, 结果显示部分化合物(2d, 2e)的抗菌活性明显增强.

关键词: 1,3,4-噻二唑, 环糊精, 合成, 抗菌活性

Abstract: Five kinds of novel β-cyclodextrin derivatives modified by thiadiazole were synthesized by the reaction of 5-alkyl-2-amino-1,3,4-thiadiazole and mono-6-deoxy-6-(p-tolylsulfonyl)-β-cyclodextrin at 80 ℃ under a nitrogen atmosphere for 2 d. The method had high yields and good separation effect. The structures of the compounds were confirmed by IR, 1H NMR, 13C NMR, UV, MS and elemental analysis. In 1H NMR spectra of cyclodextrin modified by 2-amino-1,3,4-thiadiazole, it was found that the chemical shift of thiadiazole ring shifted to upfield due to diamagnetic shielding effect caused by cyclodextrin. Other spectroscopic results were also in accordance with the theoretical value. The results indicate that this method affords a general way to synthesize β-cyclodextrin derivatives modified by thiadiazole. The biological activities of compounds 1 and 2 were screened. The results show that some compounds(2d, 2e) have strong antibacterial activities.

Key words: 1,3,4-Thiadiazole, Cyclodextrin, Synthesis, Antibacterial activity

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