2,5-bis(3-cyanophenyl)-3,4-dimethylfuran | 801223-71-2

• 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)-3,4-dimethylfuran
• 英文别名: 3-[5-(3-Cyanophenyl)-3,4-dimethylfuran-2-yl]benzonitrile
• CAS: 801223-71-2
• 化学式: C₂₀H₁₄N₂O
• 分子量: 298.344
• InChiKey: HPOVQBNHDRBYHH-UHFFFAOYSA-N

物化性质

• 熔点：
  189-191 °C
• 沸点：
  432.1±45.0 °C(Predicted)
• 密度：
  1.22±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.1
• 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)-3,4-dimethylfuran 在 盐酸 作用下， 以 乙醇 为溶剂， 反应 156.0h， 生成 2,5-bis[3-(2-imidazolinophenyl)]-3,4-dimethylfuran
  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：

  间溴苯甲醛 在 lithium aluminium tetrahydride 、 3-benzyl-5-(2-hydroxyethyl)thiazolium chloride 、 硫酸 、 氢溴酸 、 sodium acetate 、 乙酸酐 作用下， 以 四氢呋喃 、 N-甲基吡咯烷酮 、 乙醚 、 乙醇 、 溶剂黄146 为溶剂， 生成 2,5-bis(3-cyanophenyl)-3,4-dimethylfuran
  参考文献：
  名称：

  Discovery of new G-quadruplex binding chemotypes

  摘要：

  我们报告了一种新颖的基于呋喃的低分子量化学类型，具有高G-四链体亲和力和强效的抗增殖活性。

  DOI：

  10.1039/c3cc48616h

文献信息

• Discovery of new G-quadruplex binding chemotypes
  作者：Stephan A. Ohnmacht、Ehsan Varavipour、Rupesh Nanjunda、Ingrida Pazitna、Gloria Di Vita、Mekala Gunaratnam、Arvind Kumar、Mohamed A. Ismail、David W. Boykin、W. David Wilson、Stephen Neidle

  DOI：10.1039/c3cc48616h

  日期：——

  We report a novel furan-based low molecular weight chemotype with high G-quadruplex affinity and potent anti-proliferative activity.

  我们报告了一种新颖的基于呋喃的低分子量化学类型，具有高G-四链体亲和力和强效的抗增殖活性。
• 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.