2,5-bis-(3-cyanophenyl) thiophene | 186391-33-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2,5-bis-(3-cyanophenyl) thiophene
• 英文别名: 2,5-bis(3-cyanophenyl)thiophene；2,5-di-(3-cyanophenyl)thiophene；3-[5-(3-Cyanophenyl)thiophen-2-yl]benzonitrile
• CAS: 186391-33-3
• 化学式: C₁₈H₁₀N₂S
• 分子量: 286.357
• InChiKey: AOQYDQZVFFJPLD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 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：
  75.8
• 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) thiophene 在 盐酸 作用下， 以 乙醇 为溶剂， 反应 144.0h， 生成 2,5-bis-3-[(N-(4-N,N-dimethylaminobutyl)amidino)]phenylthiophene
  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
• 作为产物：
  描述：

  间溴苯甲醛 在 劳森试剂 、 N-甲基吡咯烷酮 、 3-benzyl-5-(2-hydroxyethyl)thiazolium chloride 、 sodium acetate 作用下， 以 乙醇 、 苯 为溶剂， 反应 22.0h， 生成 2,5-bis-(3-cyanophenyl) thiophene
  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

• Small molecule inhibition of RNA/ligand binding
  申请人：Scriptgen Pharmaceuticals, Inc.

  公开号：US05668165A1

  公开（公告）日：1997-09-16

  Disclosed is a method for the inhibition of binding of a ligand to an RNA, the inhibition being mediated by a small organic molecule that binds to the RNA, thereby inhibiting ligand binding. A preferred class of small organic molecules are compounds exemplified by 2,5-Bis[3-(2-N,N-dimethylaminopropylamidino)phenyl]furan.

  揭示了一种抑制配体与RNA结合的方法，该抑制是由结合到RNA的小有机分子介导的，从而抑制配体结合。一种首选的小有机分子类别是由2,5-双[3-(2-N,N-二甲基氨基丙基氨基)苯基]呋喃化合物为例。
• Structural Selectivity of Aromatic Diamidines
  作者：Jonathan B. Chaires、Jinsong Ren、Donald Hamelberg、Arvind Kumar、Vandna Pandya、David W. Boykin、W. David Wilson

  DOI：10.1021/jm049491e

  日期：2004.11.1

  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.
• 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
• US5668165A
  申请人：——

  公开号：US5668165A

  公开（公告）日：1997-09-16
• US6020488A
  申请人：——

  公开号：US6020488A

  公开（公告）日：2000-02-01