3-[[2-Pyridin-4-yl-6-(trifluoromethyl)pyrimidin-4-yl]amino]phenol | 746599-28-0

• 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: 3-[[2-Pyridin-4-yl-6-(trifluoromethyl)pyrimidin-4-yl]amino]phenol
• CAS: 746599-28-0
• 化学式: C₁₆H₁₁F₃N₄O
• 分子量: 332.285
• InChiKey: LYFVGQPLRDLNCA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  70.9
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  4-chloro-2-(4-pyridyl)-6-(trifluoromethyl)pyrimidine 、 3-氨基苯酚 在 盐酸 作用下， 以 水 为溶剂， 生成 3-[[2-Pyridin-4-yl-6-(trifluoromethyl)pyrimidin-4-yl]amino]phenol
  参考文献：
  名称：

  Discovery of substituted 4-anilino-2-arylpyrimidines as a new series of apoptosis inducers using a cell- and caspase-based high throughput screening assay. 2. Structure–activity relationships of the 2-aryl group

  摘要：

  As a continuation of our efforts to discover and develop the apoptosis inducing 4-anilino-2-(2-pyridyl) pyrimidines as potential anticancer agents, we explored replacing the 2-pyridyl group by other aryl groups. SAR studies showed that the 2-pyridyl group can be replaced by a 3-pyridyl, 4-pyridyl and 2-pyrazinyl group, and that the SAR for the anilino group was similar to that of the 2-pyridyl series. However, replacement of the 2-pyridyl group by a phenyl group, a 3,5-dichloro-4-pyridyl group, or a saturated ring led to inactive compounds. Several potent compounds, including 2f, 3d, 3j and 4a, with EC50 values of 0.048-0.024 mu M in the apoptosis induction assay against T47D cells, were identified through the SAR studies. In a tubulin polymerization assay, compound 2f, which was active against all the three cell lines tested (T47D, HTC116 and SNU398), inhibited tubulin polymerization with an IC50 value of 0.5 mu M, while compound 2a, which was active against T47D cells but not active against HTC116 and SNU398 cells, was not active in the tubulin assay at up to 50 mu M. (c) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.02.074

文献信息

• Discovery of substituted 4-anilino-2-arylpyrimidines as a new series of apoptosis inducers using a cell- and caspase-based high throughput screening assay. 2. Structure–activity relationships of the 2-aryl group
  作者：Nilantha Sirisoma、Azra Pervin、Bao Nguyen、Candace Crogan-Grundy、Shailaja Kasibhatla、Ben Tseng、John Drewe、Sui Xiong Cai

  DOI：10.1016/j.bmcl.2009.02.074

  日期：2009.4

  As a continuation of our efforts to discover and develop the apoptosis inducing 4-anilino-2-(2-pyridyl) pyrimidines as potential anticancer agents, we explored replacing the 2-pyridyl group by other aryl groups. SAR studies showed that the 2-pyridyl group can be replaced by a 3-pyridyl, 4-pyridyl and 2-pyrazinyl group, and that the SAR for the anilino group was similar to that of the 2-pyridyl series. However, replacement of the 2-pyridyl group by a phenyl group, a 3,5-dichloro-4-pyridyl group, or a saturated ring led to inactive compounds. Several potent compounds, including 2f, 3d, 3j and 4a, with EC50 values of 0.048-0.024 mu M in the apoptosis induction assay against T47D cells, were identified through the SAR studies. In a tubulin polymerization assay, compound 2f, which was active against all the three cell lines tested (T47D, HTC116 and SNU398), inhibited tubulin polymerization with an IC50 value of 0.5 mu M, while compound 2a, which was active against T47D cells but not active against HTC116 and SNU398 cells, was not active in the tubulin assay at up to 50 mu M. (c) 2009 Elsevier Ltd. All rights reserved.