5'-(4-cyanophenyl)-2,2'-bifuran-5-carbonitrile | 915979-04-3

• 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: 5'-(4-cyanophenyl)-2,2'-bifuran-5-carbonitrile
• 英文别名: 5-[5-(4-cyanophenyl)furan-2-yl]furan-2-carbonitrile
• CAS: 915979-04-3
• 化学式: C₁₆H₈N₂O₂
• 分子量: 260.252
• InChiKey: NSUISAMQZYAUJL-UHFFFAOYSA-N

物化性质

• 熔点：
  194-195 °C(Solv: N,N-dimethylformamide (68-12-2))
• 沸点：
  441.6±45.0 °C(Predicted)
• 密度：
  1.34±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  20
• 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：
  73.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5'-(4-cyanophenyl)-2,2'-bifuran-5-carbonitrile 在 盐酸羟胺 、 potassium tert-butylate 、 溶剂黄146 作用下， 以 二甲基亚砜 为溶剂， 生成 N-acetoxy-5'-[4-(N-acetoxyamidino)-phenyl]-2,2'-bifuran-5-carboxamidine
  参考文献：
  名称：

  Dicationic phenyl-2,2′-bichalcophenes and analogues as antiprotozoal agents

  摘要：

  A series of phenyl-2,2'-bichalcophene diamidines 1a-h were synthesized from the corresponding dinitriles either via a direct reaction with LiN(TMS)(2), followed by deprotection with ethanolic HCl or through the bis-O-acetoxyamidoxime followed by hydrogenation in acetic acid and EtOH over Pd-C. These diamidines show a wide range of DNA affinities as judged from their Delta T-m values which are remarkably sensitive to replacement of a furan unit with a thiophene one. These differences are explained in terms of the effect of subtle changes in geometry of the diamidines on binding efficacy. Five of the eight compounds were highly active (below 6 nM IC50) in vitro against Trypanosoma brucei rhodesiense (T. b. r.) and four gave IC(50)values less than 7 nM against Plasmodium falciparum (P. f.). Only one of the compounds was as effective as reference compounds in the T. b. r. mouse model for the acute phase of African trypanosomiasis. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.11.047
• 作为产物：
  描述：

  4-(5-bromofuran-2-yl)benzonitrile 在 四(三苯基膦)钯 N-溴代丁二酰亚胺(NBS) 作用下， 以 1,4-二氧六环 、 N,N-二甲基甲酰胺 为溶剂， 反应 48.0h， 生成 5'-(4-cyanophenyl)-2,2'-bifuran-5-carbonitrile
  参考文献：
  名称：

  Ismail, Mohamed A., Journal of Chemical Research, 2006, # 11, p. 733 - 737

  摘要：

  DOI：

文献信息

• Dicationic compounds which selectively recognize G-quadruplex DNA
  申请人：UNIVERSITY OF NORTH CAROLINA AT CHAPEL HILL

  公开号：EP1792613A3

  公开（公告）日：2007-07-25

  Dicationic compounds that are highly selective for binding G-quadruplex DNA are described. Several compounds exhibit groove binding toward G-quadruplex DNA and in vitro and in vivo activity versus Trypanosoma brucei rhodesiense. The compounds represent novel drugs for the treatment of cancer, malaria, leishmania, and trypanosomiasis.

  描述了对结合G-四链体DNA高度选择性的二阳离子化合物。几种化合物对G-四链体DNA表现出沟槽结合，并在体外和体内对布鲁氏锥虫的活性。这些化合物代表了治疗癌症、疟疾、利什曼病和锥虫病的新型药物。
• Novel bichalcophenes and their prodrugs as antiprotozoal agents
  申请人：Tidwell R. Richard

  公开号：US20060293540A1

  公开（公告）日：2006-12-28

  Novel dicationic bichalcophene compounds are described. The presently disclosed novel dicationic bichalcophene compounds exhibit in vitro activity versus Trypanosoma brucei rhodesiense, Plasmodium falciparum , or Leishmania donovani comparable to that of pentamidine and furamidine. Some of the novel dicationic bichalcophene compounds displayed good activity in vivo in a murine model of a Trypanosoma brucei rhodesiense infection.

  本文描述了新型的双阳离子双硫杂环化合物。目前披露的新型双阳离子双硫杂环化合物在体外对Trypanosoma brucei rhodesiense、Plasmodium falciparum或Leishmania donovani的活性与pentamidine和furamidine相当。其中一些新型双阳离子双硫杂环化合物在小鼠Trypanosoma brucei rhodesiense感染模型中表现出良好的活性。
• Bichalcophenes and their prodrugs as antiprotozoal agents
  申请人：The University of North Carolina at Chapel Hill

  公开号：US07517893B2

  公开（公告）日：2009-04-14

  Novel dicationic bichalcophene compounds are described. The presently disclosed novel dicationic bichalcophene compounds exhibit in vitro activity versus Trypanosoma brucei rhodesiense, Plasmodium falciparum, or Leishmania donovani comparable to that of pentamidine and furamidine. Some of the novel dicationic bichalcophene compounds displayed good activity in vivo in a murine model of a Trypanosoma brucei rhodesiense infection.

  本文描述了新型二阳离子双硫化物化合物。目前披露的新型二阳离子双硫化物化合物在体外对Trypanosoma brucei rhodesiense、Plasmodium falciparum或Leishmania donovani的活性与pentamidine和furamidine相当。其中一些新型二阳离子双硫化物化合物在Trypanosoma brucei rhodesiense感染小鼠模型中显示出良好的体内活性。
• 5,5'-bis-(4-amidinophenyl)-2,2'-bifuran derivatives and related compounds as antiprotozoal agent and prodrugs thereof
  申请人：The University of North Carolina at Chapel Hill

  公开号：EP1726589B1

  公开（公告）日：2008-10-15
• US7517893B2
  申请人：——

  公开号：US7517893B2

  公开（公告）日：2009-04-14