3-({4-[4-(methanesulfonyl)phenyl]pyrimidin-2-yl}amino)benzamide | 1128095-86-2

• 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-({4-[4-(methanesulfonyl)phenyl]pyrimidin-2-yl}amino)benzamide
• 英文别名: 3-(4-(4-(methylsulfonyl)phenyl)pyrimidin-2-ylamino)benzamide；3-[[4-(4-Methylsulfonylphenyl)pyrimidin-2-yl]amino]benzamide
• CAS: 1128095-86-2
• 化学式: C₁₈H₁₆N₄O₃S
• 分子量: 368.416
• InChiKey: WKEPLPIONCNGOW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  123
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  4-（甲磺酰基）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 3-({4-[4-(methanesulfonyl)phenyl]pyrimidin-2-yl}amino)benzamide
  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

• [EN] SUBSTITUTED PYRIMIDINYL-AMINES AS PROTEIN KINASE INHIBITORS<br/>[FR] PYRIMIDINYL-AMINES SUBSTITUÉES EN TANT QU'INHIBITEURS DE LA PROTÉINE KINASE
  申请人：SCRIPPS RESEARCH INST

  公开号：WO2009032861A1

  公开（公告）日：2009-03-12

  The present invention provides novel substituted pyrimidinyl-amines that are useful as inhibitors of protein kinases, especially c-Jun N-terminal kinases (JNK) and pharmaceutical compositions thereof and methods of using the same for treating conditions responsive to the inhibition of the JNK pathway.

  本发明提供了一种新型的取代嘧啶基胺，可用作蛋白激酶抑制剂，特别是c-Jun N-末端激酶（JNK）的抑制剂，以及包含它们的药物组合物和使用相同的方法来治疗对JNK途径抑制敏感的疾病。
• SUBSTITUTED PYRIMIDINYL-AMINES AS PROTEIN KINASE INHIBITORS
  申请人：Kamenecka Theodore Mark

  公开号：US20130231336A1

  公开（公告）日：2013-09-05

  The present invention provides novel substituted pyrimidinyl-amines that are useful as inhibitors of protein kinases, especially c-Jun N-terminal kinases (JNK) and pharmaceutical compositions thereof and methods of using the same for treating conditions responsive to the inhibition of the JNK pathway.

  本发明提供了一种新型的取代嘧啶基胺，可用作蛋白激酶抑制剂，特别是c-Jun N末端激酶（JNK）的抑制剂，以及其药物组合物和使用同样治疗对JNK通路抑制有响应的疾病的方法。
• US8530480B2
  申请人：——

  公开号：US8530480B2

  公开（公告）日：2013-09-10
• US9018205B2
  申请人：——

  公开号：US9018205B2

  公开（公告）日：2015-04-28
• 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.