(E)-N-(3-chloro-4-fluorophenyl)-4-methyl-3-(3-(pyrimidin-5-yl)acrylamido)benzamide | 1393911-21-1

• 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: (E)-N-(3-chloro-4-fluorophenyl)-4-methyl-3-(3-(pyrimidin-5-yl)acrylamido)benzamide
• 英文别名: N-(3-chloro-4-fluorophenyl)-4-methyl-3-[[(E)-3-pyrimidin-5-ylprop-2-enoyl]amino]benzamide
• CAS: 1393911-21-1
• 化学式: C₂₁H₁₆ClFN₄O₂
• 分子量: 410.835
• InChiKey: DLICNBDXFXRCRL-XVNBXDOJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  29
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  84
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  4-甲基-3-硝基苯甲酸 在 氯化亚砜 、 铁粉 、 氯化铵 、 三乙胺 作用下， 以 乙醇 、 二氯甲烷 、 水 为溶剂， 生成 (E)-N-(3-chloro-4-fluorophenyl)-4-methyl-3-(3-(pyrimidin-5-yl)acrylamido)benzamide
  参考文献：
  名称：

  Design, synthesis and biological evaluation of novel acrylamide analogues as inhibitors of BCR–ABL kinase

  摘要：

  A series of acrylamide analogues were designed and synthesized from Imatinib and Nilotinib as novel BCR-ABL inhibitors by application of the principle of nonclassical electronic isostere. All new compounds were evaluated for their inhibitory effects on the activity of BCR-ABL kinase and the proliferation of K562 leukemia cancer cells in vitro. The acrylamide analogues in which the substituent in C ring was trifluoromethyl group were identified as highly potent BCR-ABL kinase inhibitors. Compound 13f exhibited an IC50 value as low as 20.6 nM in ABL kinase inhibition and an IC50 value of 32.3 nM for antiproliferative activity, about 10.5-fold and 12-fold lower than those of Imatinib respectively. These results suggest that compound 13f is a promising candidate as a novel BCR-ABL kinase inhibitor for further development. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.06.044

文献信息

• Acrylamide Derivative And Use Thereof In Manufacture Of Medicament
  申请人：Sun Shuping

  公开号：US20120116075A1

  公开（公告）日：2012-05-10

  An acrylamide derivative represented by formula (I), pharmaceutically acceptable salts and solvates thereof, as well as a medicament containing said acrylamide derivative or its pharmaceutically acceptable salts as the active ingredient, which can be used to treat disorders associated with tyrosine kinase especially Bcr-Abl, including proliferative disorders such as cancers, and inflammation and the like are provided.

  由公式(I)表示的丙烯酰胺衍生物，其药学上可接受的盐和溶剂，以及包含该丙烯酰胺衍生物或其药学上可接受的盐作为活性成分的药物剂，可用于治疗与酪氨酸激酶尤其是Bcr-Abl相关的紊乱，包括增生性疾病如癌症、炎症等。
• US8426446B2
  申请人：——

  公开号：US8426446B2

  公开（公告）日：2013-04-23