(S)-N-(4-chloro-5-(2,4,6-trifluorophenyl)-6-((1,1,1-trifluoropropan-2-yl)amino)pyrimidin-2-yl)-N-methylcyanamide | 879325-04-9

• 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: (S)-N-(4-chloro-5-(2,4,6-trifluorophenyl)-6-((1,1,1-trifluoropropan-2-yl)amino)pyrimidin-2-yl)-N-methylcyanamide
• CAS: 879325-04-9
• 化学式: C₁₅H₁₀ClF₆N₅
• 分子量: 409.721
• InChiKey: RHRFJMVDMARPOB-LURJTMIESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.49
• 重原子数：
  27.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  64.84
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (S)-N-(4-chloro-5-(2,4,6-trifluorophenyl)-6-((1,1,1-trifluoropropan-2-yl)amino)pyrimidin-2-yl)-N-methylcyanamide 、 3-二甲氨基-1-丙醇 在 sodium hydride 作用下， 以 二甲基亚砜 为溶剂， 生成 (4-chloro-5-{4-[3-(dimethylamino)propoxy]-2,6-difluorophenyl}-6-{[(1S)-2,2,2-trifluoro-1-methylethyl]amino}pyrimidin-2-yl)methylcyanamide
  参考文献：
  名称：

  2-Cyanoaminopyrimidines as a class of antitumor agents that promote tubulin polymerization

  摘要：

  A series of 4-chloro-2-cyanoamino-6-fluoroalkylamino-5-phenylpyrimidines was prepared as a result of our efforts to modify a series of [1,2,4]triazolo[1,5-a]pyrimidines that proved to be potent anticancer agents with a unique mechanism of tubulin inhibition. On the cyanoamino nitrogen, a methyl group is optimal for activity among alkyl groups introduced. The structure-activity relationship for the rest of the molecule resembles that of [1,2,4]triazolo[1,5-a]pyrimidines. A lead compound (5) retained in vitro potency compared with TTI-237. In the mechanism of action studies, it behaved in the same manner as TTI-237. In addition, it is also capable of overcoming multidrug resistance due to P-gp. These findings strongly suggest that this series of 2-cyanoaminopyrimidines binds at the same site and in the same binding mode as TTI-237. Further modifications of the 2-cyanoamino group are underway. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.03.070
• 作为产物：
  描述：

  在 sodium hydride 作用下， 以 二甲基亚砜 为溶剂， 生成 (S)-N-(4-chloro-5-(2,4,6-trifluorophenyl)-6-((1,1,1-trifluoropropan-2-yl)amino)pyrimidin-2-yl)-N-methylcyanamide
  参考文献：
  名称：

  2-Cyanoaminopyrimidines as a class of antitumor agents that promote tubulin polymerization

  摘要：

  A series of 4-chloro-2-cyanoamino-6-fluoroalkylamino-5-phenylpyrimidines was prepared as a result of our efforts to modify a series of [1,2,4]triazolo[1,5-a]pyrimidines that proved to be potent anticancer agents with a unique mechanism of tubulin inhibition. On the cyanoamino nitrogen, a methyl group is optimal for activity among alkyl groups introduced. The structure-activity relationship for the rest of the molecule resembles that of [1,2,4]triazolo[1,5-a]pyrimidines. A lead compound (5) retained in vitro potency compared with TTI-237. In the mechanism of action studies, it behaved in the same manner as TTI-237. In addition, it is also capable of overcoming multidrug resistance due to P-gp. These findings strongly suggest that this series of 2-cyanoaminopyrimidines binds at the same site and in the same binding mode as TTI-237. Further modifications of the 2-cyanoamino group are underway. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.03.070