2,5-di(4-azidobutyl)thiophene | 233748-12-4

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: 2,5-di(4-azidobutyl)thiophene
• CAS: 233748-12-4
• 化学式: C₁₂H₁₈N₆S
• 分子量: 278.381
• InChiKey: NGZVHYHBJWEFQM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.01
• 重原子数：
  19.0
• 可旋转键数：
  10.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  97.52
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  2,5-di(4-azidobutyl)thiophene 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 8.0h， 生成 2,5-di(4-(3-dodecylureido)butyl)thiophene
  参考文献：
  名称：

  Efficient Intermolecular Charge Transport in Self-Assembled Fibers of Mono- and Bithiophene Bisurea Compounds

  摘要：

  Hydrogen bonds between urea units allow self-organization of π systems in mono- and bithiophenes into fibers as shown schematically. In these fibers there is a surprisingly high mobility of charge carriers as determined by pulse-radiolysis time-resolved microwave conductivity measurements.

  DOI：

  10.1002/(sici)1521-3773(19990517)38:10<1393::aid-anie1393>3.0.co;2-h
• 作为产物：
  描述：

  2,5-di(4-chlorobutyl)thiophene 在 sodium azide 作用下， 以 二甲基亚砜 为溶剂， 以99%的产率得到2,5-di(4-azidobutyl)thiophene
  参考文献：
  名称：

  Efficient Intermolecular Charge Transport in Self-Assembled Fibers of Mono- and Bithiophene Bisurea Compounds

  摘要：

  Hydrogen bonds between urea units allow self-organization of π systems in mono- and bithiophenes into fibers as shown schematically. In these fibers there is a surprisingly high mobility of charge carriers as determined by pulse-radiolysis time-resolved microwave conductivity measurements.

  DOI：

  10.1002/(sici)1521-3773(19990517)38:10<1393::aid-anie1393>3.0.co;2-h

文献信息

• Oligothiophene compounds inhibit the membrane fusion between H5N1 avian influenza virus and the endosome of host cell
  作者：Zhibo Zhu、Zhili Yao、Xiantian Shen、Zhipeng Chen、Xiangtao Liu、Jon R. Parquette、Shuwen Liu

  DOI：10.1016/j.ejmech.2017.02.040

  日期：2017.4

  Hemagglutinin (HA) which is essential for influenza viral infection and replication has become a target for the design of anti-influenza drugs. A novel series of oligothiophene compounds focused on the target were synthesized as specific inhibitors against the H5 subtype of influenza A viruses because oligothiophene has Pi-Pi stronger pep interactions with residues F110(2) and M24(1) of HA2 side chains. Oligothiophene compounds were designed and synthesized by a series of alkylation, azidation, amination and amidation reactions. The entry inhibitory activities of those compounds were tested at a cellular level against H5N1 influenza pseudovirus. Compound 3sf was revealed as the most active inhibitor in this series with an IC50 of 0.029 mM. The activity of 3sf is almost 1000 times that of the positive reference compound (CL-385319). A structure-activity analysis of these compounds demonstrated that the size of the oligothiophene compounds was very important for the inhibitory activity. Four compounds (3sk, 3sf, 3sc and 4sc) of strong inhibitiory activity against H5N1 influenza pseudovirus were assessed against H1N1 influenza virus MDCK. They also showed strong inhibitiory activity with IC50s of 3.292 mu M, 1.240 mu M, 1.119 mu M and 0.768 mu M, respectively. (C) 2017 Elsevier Masson SAS. All rights reserved.