4,6-bis(4-ethylmercaptophenyl)pyrimidine

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 4,6-bis(4-ethylmercaptophenyl)pyrimidine
• 英文别名: 4,6-Bis(4-ethylsulfanylphenyl)pyrimidine
• 化学式: C₂₀H₂₀N₂S₂
• 分子量: 352.524
• InChiKey: HOVIKKZXZQJILJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  76.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  4,6-bis(4-bromophenyl)pyrimidine 、 乙硫醇钠 以 N,N-二甲基甲酰胺 为溶剂， 反应 48.0h， 以62%的产率得到4,6-bis(4-ethylmercaptophenyl)pyrimidine
  参考文献：
  名称：

  Design, Synthesis, and Evaluation of Novel Biarylpyrimidines:  A New Class of Ligand for Unusual Nucleic Acid Structures

  摘要：

  Biarylpyrimidines are characterized as selective ligands for higher-order nucleic acid structures. A concise and efficient synthesis has been devised incorporating Suzuki biaryl cross-coupling of dihalopyrimidines. Two ligand series are described based on the parent thioether 4,6-bis[4-[[2-(dimethylamino)ethyl]mercapto]phenyl] pyrimidine (1a) and amide 4,6-bis(4[(2-(dimethylamino) ethyl) carboxamido] phenyl) pyrimidine (2a) compounds. In UV thermal denaturation studies with the poly(dA),[poly(dT)](2) triplex structure, thioethers showed stabilization of the triplex form (Delta T-m <= 20 degrees C). In contrast, amides showed duplex stabilization (Delta T-m <= 15 degrees C) and either negligible stabilization or specific destabilization (Delta T-m = 5 degrees C) of the triplex structure. Full spectra of nucleic acid binding preferences were determined by competition dialysis. The strongest interacting thioether bound preferentially to the poly(dA)(.)[poly(dT)](2) triplex, Kapp) 1.6 x 10(5) M-1 (40 x Kapp for CT DNA duplex). In contrast, the strongest binding amide selected the (T(2)G(20)T(2)) 4 quadruplex structure, Kapp) 0.31 x 10(5) M-1 (6.5 x K-app for CT DNA duplex).

  DOI：

  10.1021/jm060315a

文献信息

• Design, Synthesis, and Evaluation of Novel Biarylpyrimidines:  A New Class of Ligand for Unusual Nucleic Acid Structures
  作者：Richard T. Wheelhouse、Sharon A. Jennings、Victoria A. Phillips、Dimitrios Pletsas、Peter M. Murphy、Nichola C. Garbett、Jonathan B. Chaires、Terence C. Jenkins

  DOI：10.1021/jm060315a

  日期：2006.8.1

  Biarylpyrimidines are characterized as selective ligands for higher-order nucleic acid structures. A concise and efficient synthesis has been devised incorporating Suzuki biaryl cross-coupling of dihalopyrimidines. Two ligand series are described based on the parent thioether 4,6-bis[4-[[2-(dimethylamino)ethyl]mercapto]phenyl] pyrimidine (1a) and amide 4,6-bis(4[(2-(dimethylamino) ethyl) carboxamido] phenyl) pyrimidine (2a) compounds. In UV thermal denaturation studies with the poly(dA),[poly(dT)](2) triplex structure, thioethers showed stabilization of the triplex form (Delta T-m <= 20 degrees C). In contrast, amides showed duplex stabilization (Delta T-m <= 15 degrees C) and either negligible stabilization or specific destabilization (Delta T-m = 5 degrees C) of the triplex structure. Full spectra of nucleic acid binding preferences were determined by competition dialysis. The strongest interacting thioether bound preferentially to the poly(dA)(.)[poly(dT)](2) triplex, Kapp) 1.6 x 10(5) M-1 (40 x Kapp for CT DNA duplex). In contrast, the strongest binding amide selected the (T(2)G(20)T(2)) 4 quadruplex structure, Kapp) 0.31 x 10(5) M-1 (6.5 x K-app for CT DNA duplex).