2,5-bis(3-cyanophenyl)furan | 186391-32-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 呋喃
• 英文名称: 2,5-bis(3-cyanophenyl)furan
• 英文别名: 3-[5-(3-Cyanophenyl)furan-2-yl]benzonitrile
• CAS: 186391-32-2
• 化学式: C₁₈H₁₀N₂O
• 分子量: 270.29
• InChiKey: PMROPIKAJGRESR-UHFFFAOYSA-N

物化性质

• 熔点：
  230-233 °C
• 沸点：
  460.1±45.0 °C(Predicted)
• 密度：
  1.27±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  60.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2,5-bis(3-cyanophenyl)furan 在 盐酸 、 氨 作用下， 以 乙醇 为溶剂， 反应 156.0h， 生成 2,5-bis(3-amidinophenyl)furan
  参考文献：
  名称：

  Structural Selectivity of Aromatic Diamidines

  摘要：

  Competition dialysis was used to study the interactions of 13 substituted aromatic diamidine compounds with 13 nucleic acid structures and sequences. The results show a striking selectivity of these compounds for the triplex structure poly dA:(poly dT)(2), a novel aspect of their interaction with nucleic acids not previously described. The triplex selectivity of selected compounds was confirmed by thermal denaturation studies. Triplex selectivity was found to be modulated by the location of amidine substiuents on the core phenyl-furan-phenyl ring scaffold. Molecular models were constructed to rationalize the triplex selectivity of DB359, the most selective compound in the series. Its triplex selectivity was found to arise from optimal ring stacking on base triplets, along with proper positioning of its amidine substituents to occupy the minor and the major-minor grooves of the triplex. New insights into the molecular recognition of nucleic acid structures emerged from these studies, adding to the list of available design principles for selectively targeting DNA and RNA.

  DOI：

  10.1021/jm049491e
• 作为产物：
  描述：

  1,4-di(3-cyanophenyl)butanedione 生成 2,5-bis(3-cyanophenyl)furan
  参考文献：
  名称：

  Inhibition of the HIV-1 rev–RRE complex formation by unfused aromatic cations

  摘要：

  RNA viruses cause a wide range of human diseases. Development of new agents to target such viruses is an active area of research. Towards this goal, a series of diphenylfuran cations as potential inhibitors of the Rev-RRE complex have been designed and synthesized. Analysis of the interaction of the diphenylfurans with RRE and TAR RNA model systems by gel shift assays indicates that they exhibit both sequence and structure-dependent binding modes. Our results show a strong interaction between the diphenylfuran ring system and RRE bases, while the TAR interactions are much weaker with the compounds that are the best inhibitors of Rev-RRE. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(00)00344-8

文献信息

• Discovery of Small Molecule Ligands for MALAT1 by Tuning an RNA‐Binding Scaffold
  作者：Anita Donlic、Brittany S. Morgan、Jason L. Xu、Anqi Liu、Carlos Roble、Amanda E. Hargrove

  DOI：10.1002/anie.201808823

  日期：2018.10

  and high levels of MALAT1 are found in several cancers. Here, we synthesize a small molecule library based on an RNA‐binding scaffold, diphenylfuran (DPF), screen it against a variety of nucleic acid constructs, and demonstrate for the first time that the MALAT1 triple helix can be selectively targeted with small molecules. Computational analysis revealed a trend between subunit positioning and composition

  致癌性长非编码RNA转移相关肺腺癌转录本1（MALAT1）3'-末端的结构研究证实了独特的三螺旋结构。这种结构能够使转录物积累，并且在几种癌症中发现了高水平的MALAT1。在这里，我们基于RNA结合支架二苯呋喃（DPF）合成了一个小分子文库，针对各种核酸构建体进行了筛选，并首次证明MALAT1三重螺旋可以选择性地靶向小分子。计算分析表明，DPF形状和分子内相互作用的亚基定位和组成之间存在趋势，而反过来通常与选择性和结合强度相关。
• Antifungal activity of dicationic molecules
  申请人：UNIVERSITY OF NORTH CAROLINA AT CHAPEL HILL

  公开号：EP1685836A2

  公开（公告）日：2006-08-02

  Methods of treating fungal infections comprise administering a therapeutically effective amount of a compound described by Formulas [(I)-(II)]. Examples of fungal infections include Candida albicans, Cryptococcus neoformans, Aspergillus fumigatus, Fusarium solani, and combinations thereof.

  治疗真菌感染的方法包括施用治疗有效量的式[(I)-(II)]所述化合物。真菌感染的例子包括白色念珠菌、新生隐球菌、烟曲霉、梭菌及其组合。
• SMALL MOLECULE INHIBITION OF RNA/LIGAND BINDING
  申请人：SCRIPTGEN PHARMACEUTICALS, INC.

  公开号：EP0833824A2

  公开（公告）日：1998-04-08
• ANTIFUNGAL ACTIVITY OF DICATIONIC MOLECULES
  申请人：UNIVERSITY OF NORTH CAROLINA AT CHAPEL HILL

  公开号：EP1143959A2

  公开（公告）日：2001-10-17
• US5668165A
  申请人：——

  公开号：US5668165A

  公开（公告）日：1997-09-16