1-(4-bromophenyl)-4-(3-bromophenyl)butane-1,4-dione | 801223-74-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(4-bromophenyl)-4-(3-bromophenyl)butane-1,4-dione
• 英文别名: 1-(3-Bromophenyl)-4-(4-bromophenyl)butane-1,4-dione
• CAS: 801223-74-5
• 化学式: C₁₆H₁₂Br₂O₂
• 分子量: 396.078
• InChiKey: BYJGWEMLPORGEY-UHFFFAOYSA-N

物化性质

• 熔点：
  118-119 °C
• 沸点：
  500.1±45.0 °C(Predicted)
• 密度：
  1.611±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(4-bromophenyl)-4-(3-bromophenyl)butane-1,4-dione 在 盐酸 作用下， 以 甲醇 、 氯仿 为溶剂， 反应 2.0h， 以89%的产率得到2-(4-bromophenyl)-5-(3-bromophenyl)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：

  间溴苯甲醛 、 3-二甲氨基-4'-溴苯丙酮盐酸盐 在 3-苄基羟乙基甲基噻唑氯化锂 、 三乙胺 作用下， 以 1,4-二氧六环 为溶剂， 反应 12.0h， 以40%的产率得到1-(4-bromophenyl)-4-(3-bromophenyl)butane-1,4-dione
  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

文献信息

• 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.