4,6-bis(4-methoxycarbonylphenyl)pyrimidine | 609355-99-9

• 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-methoxycarbonylphenyl)pyrimidine
• 英文别名: methyl 4-[6-(4-methoxycarbonylphenyl)pyrimidin-4-yl]benzoate
• CAS: 609355-99-9
• 化学式: C₂₀H₁₆N₂O₄
• 分子量: 348.358
• InChiKey: NGEUNOTZEOBNQH-UHFFFAOYSA-N

物化性质

• 熔点：
  223.5-225.0 °C(Solv: ethyl acetate (141-78-6))
• 沸点：
  531.4±50.0 °C(Predicted)
• 密度：
  1.234±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.38
• 重原子数：
  26.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  78.38
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  4,6-bis(4-methoxycarbonylphenyl)pyrimidine 在 sodium hydroxide 作用下， 以100%的产率得到4,6-二(4-羧苯基)嘧啶
  参考文献：
  名称：

  Biarylpyrimidines: a new class of ligand for high-order DNA recognitionElectronic supplementary information (ESI) available: experimental details of UV melting studies and example spectroscopic and analytical data. See http://www.rsc.org/suppdata/cc/b3/b301554h/

  摘要：

  具有ω-氨基烷基取代基的联苯嘧啶类化合物已被设计为高阶DNA结构的配体：分光光度法、热学法及竞争平衡透析法检测显示，将取代基连接的功能基团由硫醚改为酰胺，可使其结构结合偏好从三链DNA转变为四链DNA；新型的配体无毒且对人类端粒酶具有中等抑制作用。

  DOI：

  10.1039/b301554h
• 作为产物：
  描述：

  4,6-二碘嘧啶 、 4-甲氧羰基苯硼酸 在 四(三苯基膦)钯 potassium carbonate 作用下， 以 甲醇 、 甲苯 为溶剂， 以91%的产率得到4,6-bis(4-methoxycarbonylphenyl)pyrimidine
  参考文献：
  名称：

  Biarylpyrimidines: a new class of ligand for high-order DNA recognitionElectronic supplementary information (ESI) available: experimental details of UV melting studies and example spectroscopic and analytical data. See http://www.rsc.org/suppdata/cc/b3/b301554h/

  摘要：

  具有ω-氨基烷基取代基的联苯嘧啶类化合物已被设计为高阶DNA结构的配体：分光光度法、热学法及竞争平衡透析法检测显示，将取代基连接的功能基团由硫醚改为酰胺，可使其结构结合偏好从三链DNA转变为四链DNA；新型的配体无毒且对人类端粒酶具有中等抑制作用。

  DOI：

  10.1039/b301554h

文献信息

• Biarylpyrimidines: a new class of ligand for high-order DNA recognitionElectronic supplementary information (ESI) available: experimental details of UV melting studies and example spectroscopic and analytical data. See http://www.rsc.org/suppdata/cc/b3/b301554h/
  作者：Peter M. Murphy、Victoria A. Phillips、Sharon A. Jennings、Nichola C. Garbett、Jonathan B. Chaires、Terence C. Jenkins、Richard T. Wheelhouse

  DOI：10.1039/b301554h

  日期：2003.4.30

  Biarylpyrimidines bearing ω-aminoalkyl substituents have been designed as ligands for high-order DNA structures: spectrophotometric, thermal and competition equilibrium dialysis assays showed that changing the functional group for substituent attachment from thioether to amide switches the structural binding preference from triplex to tetraplex DNA; the novel ligands are non-toxic and moderate inhibitors of human telomerase.

  具有ω-氨基烷基取代基的联苯嘧啶类化合物已被设计为高阶DNA结构的配体：分光光度法、热学法及竞争平衡透析法检测显示，将取代基连接的功能基团由硫醚改为酰胺，可使其结构结合偏好从三链DNA转变为四链DNA；新型的配体无毒且对人类端粒酶具有中等抑制作用。
• 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).