5,5'-di(4-azidobutyl)-2,2'-bithiophene | 233748-15-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 双噻吩和低聚噻吩
• 英文名称: 5,5'-di(4-azidobutyl)-2,2'-bithiophene
• 英文别名: 2-(4-azidobutyl)-5-(5-(4-azidobutyl)-2-thienyl)thiophene；2-(4-Azidobutyl)-5-[5-(4-azidobutyl)thiophen-2-yl]thiophene
• CAS: 233748-15-7
• 化学式: C₁₆H₂₀N₆S₂
• 分子量: 360.507
• InChiKey: DKTACBXLCGSPST-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.8
• 重原子数：
  24
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  85.2
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  5,5'-di(4-azidobutyl)-2,2'-bithiophene 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 5,5'-di(4-(3-dodecylureido)butyl)-2,2'-bithiophene
  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：

  5,5'-di(4-chlorobutyl)-2,2'-bithiophene 在 sodium azide 作用下， 以 二甲基亚砜 为溶剂， 以98%的产率得到5,5'-di(4-azidobutyl)-2,2'-bithiophene
  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

• 一种低聚噻吩衍生物及其应用
  申请人：南方医科大学

  公开号：CN104496962B

  公开（公告）日：2017-01-04

  本发明属于有机化学领域，具体涉及一种低聚噻吩衍生物，其分子结构如下式(Ⅰ)所示，式中R1是氢，3‑溴丙基，4‑溴丁基，3‑氨基丙基，4‑氨基丁基，3‑叠氮基丙基，4‑叠氮基丁基，3‑(3‑氟‑5‑(三氟甲基)苯甲酰胺基)丙基和4‑(3‑氟‑5‑(三氟甲基)苯甲酰胺基)丁基其中一种；R2是氢，3‑溴丙基，4‑溴丁基，3‑氨基丙基，4‑氨基丁基，3‑叠氮基丙基和4‑叠氮基丁基其中一种；n＝1,2,3或者4。本发明所述的低聚噻吩衍生物具有抑制流感病毒的效果。
• 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.