3-amino-4-methyl-N-[4-(trifluoromethoxy)phenyl]benzamide | 1393911-17-5

• 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: 3-amino-4-methyl-N-[4-(trifluoromethoxy)phenyl]benzamide
• CAS: 1393911-17-5
• 化学式: C₁₅H₁₃F₃N₂O₂
• 分子量: 310.276
• InChiKey: XMKYKDPUWRIZPT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  64.4
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (E)-3-(pyramidin-5-yl)acryloyl chloride hydrochloride 、 3-amino-4-methyl-N-[4-(trifluoromethoxy)phenyl]benzamide 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以86.5%的产率得到(E)-4-methyl-3-(3-(pyrimidin-5-yl)acrylamido)-N-(4-(trifluoromethoxy)phenyl)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
• 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 3-amino-4-methyl-N-[4-(trifluoromethoxy)phenyl]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

• Design, synthesis and biological evaluation of novel acrylamide analogues as inhibitors of BCR–ABL kinase
  作者：Shuxin Li、Zhenglin Yao、Yanjin Zhao、Wei Chen、Huijia Wang、Xianzhao Kuang、Wenhu Zhan、Shan Yao、Shanyou Yu、Wenxiang Hu

  DOI：10.1016/j.bmcl.2012.06.044

  日期：2012.8

  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.