methyl 4-{[4-(4-methoxyphenyl)pyrimidin-2-yl]amino}benzoate

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: methyl 4-{[4-(4-methoxyphenyl)pyrimidin-2-yl]amino}benzoate
• 英文别名: Methyl 4-[[4-(4-methoxyphenyl)pyrimidin-2-yl]amino]benzoate；methyl 4-[[4-(4-methoxyphenyl)pyrimidin-2-yl]amino]benzoate
• 化学式: C₁₉H₁₇N₃O₃
• 分子量: 335.362
• InChiKey: AXJASERJESOXNW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  73.3
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  4-甲氧基苯硼酸 在 sodium carbonate 、 三氟乙酸 作用下， 以 水 、 异丙醇 为溶剂， 反应 18.25h， 生成 methyl 4-{[4-(4-methoxyphenyl)pyrimidin-2-yl]amino}benzoate
  参考文献：
  名称：

  Synthesis and evaluation of the NSCLC anti-cancer activity and physical properties of 4-aryl- N -phenylpyrimidin-2-amines

  摘要：

  Reported herein are efforts to profile 4-aryl-N-phenylpyrimidin-2-amines in terms of their anti-cancer activity towards non small-cell lung carcinoma (NSCLC) cells. We have synthesized new 4-aryl-N-phenylpyrimidin-2-amines and assessed them in terms of their cytotoxicity (A549, NCI-H187, MCF7, Vero & KB) and physicochemical properties (logD(7.4) and solubility). 13f and 13c demonstrated potent anti-cancer activity in A549 cells (0.2 mu M), compared to 0.4 mu M for the NSCLC drug Doxorubicin. 13f also displayed low experimental logD(7.4) (2.9) and the best solubility (similar to 40 mu M). Compounds 13b and 13d showed the best balance of A549 anti-cancer activity and selectivity. 13g showed good activity and selectivity comparable with the anti-cancer drug Doxorubicin. (C) 2017 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2017.08.063

文献信息

• Synthesis and evaluation of the NSCLC anti-cancer activity and physical properties of 4-aryl- N -phenylpyrimidin-2-amines
  作者：Borvornwat Toviwek、Praphasri Suphakun、Kiattawee Choowongkomon、Supa Hannongbua、M. Paul Gleeson

  DOI：10.1016/j.bmcl.2017.08.063

  日期：2017.10

  Reported herein are efforts to profile 4-aryl-N-phenylpyrimidin-2-amines in terms of their anti-cancer activity towards non small-cell lung carcinoma (NSCLC) cells. We have synthesized new 4-aryl-N-phenylpyrimidin-2-amines and assessed them in terms of their cytotoxicity (A549, NCI-H187, MCF7, Vero & KB) and physicochemical properties (logD(7.4) and solubility). 13f and 13c demonstrated potent anti-cancer activity in A549 cells (0.2 mu M), compared to 0.4 mu M for the NSCLC drug Doxorubicin. 13f also displayed low experimental logD(7.4) (2.9) and the best solubility (similar to 40 mu M). Compounds 13b and 13d showed the best balance of A549 anti-cancer activity and selectivity. 13g showed good activity and selectivity comparable with the anti-cancer drug Doxorubicin. (C) 2017 Elsevier Ltd. All rights reserved.