(E)-3-(dimethylamino)-1-(1-ethyl-1H-indazol-3-yl)prop-2-en-1-one | 1415509-14-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡唑类
• 英文名称: (E)-3-(dimethylamino)-1-(1-ethyl-1H-indazol-3-yl)prop-2-en-1-one
• 英文别名: (E)-3-(dimethylamino)-1-(1-ethylindazol-3-yl)prop-2-en-1-one
• CAS: 1415509-14-6
• 化学式: C₁₄H₁₇N₃O
• 分子量: 243.308
• InChiKey: FWBHTEPWPFJEQV-MDZDMXLPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  38.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (E)-3-(dimethylamino)-1-(1-ethyl-1H-indazol-3-yl)prop-2-en-1-one 、 1-(3-hydroxyphenyl)guanidine 以 乙腈 为溶剂， 反应 0.67h， 以23%的产率得到3-[[4-(1-Ethylindazol-3-yl)pyrimidin-2-yl]amino]phenol
  参考文献：
  名称：

  Synthesis and biological evaluation of imidazo[4,5-b]pyridine and 4-heteroaryl-pyrimidine derivatives as anti-cancer agents

  摘要：

  A series of N-phenyl-imidazo[4,5-b]pyridin-2-amines, 4-indazolyl-N-phenylpyrimidin-2-amines and N-phenyl-4-pyrazolo[3,4-b]pyridin-pyrimidin-2-amines have been synthesized. Their anti-proliferative activities were tested in HCT-116 human colon carcinoma and MCF-7 breast carcinoma cell lines. Many exhibited potent anti-proliferative and CDK9 inhibitory activities. A lead compound 18b demonstrated the ability to reduce the level of Mcl-1 anti-apoptotic protein, to activate caspase 3/7 and induce cancer cell apoptosis. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.09.034
• 作为产物：
  描述：

  3-乙酰基吲唑 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 16.0h， 生成 (E)-3-(dimethylamino)-1-(1-ethyl-1H-indazol-3-yl)prop-2-en-1-one
  参考文献：
  名称：

  Synthesis and biological evaluation of imidazo[4,5-b]pyridine and 4-heteroaryl-pyrimidine derivatives as anti-cancer agents

  摘要：

  A series of N-phenyl-imidazo[4,5-b]pyridin-2-amines, 4-indazolyl-N-phenylpyrimidin-2-amines and N-phenyl-4-pyrazolo[3,4-b]pyridin-pyrimidin-2-amines have been synthesized. Their anti-proliferative activities were tested in HCT-116 human colon carcinoma and MCF-7 breast carcinoma cell lines. Many exhibited potent anti-proliferative and CDK9 inhibitory activities. A lead compound 18b demonstrated the ability to reduce the level of Mcl-1 anti-apoptotic protein, to activate caspase 3/7 and induce cancer cell apoptosis. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.09.034

文献信息

• Synthesis and biological evaluation of imidazo[4,5-b]pyridine and 4-heteroaryl-pyrimidine derivatives as anti-cancer agents
  作者：Pawel M. Lukasik、Sherifa Elabar、Frankie Lam、Hao Shao、Xiangrui Liu、Abdullah Y. Abbas、Shudong Wang

  DOI：10.1016/j.ejmech.2012.09.034

  日期：2012.11

  A series of N-phenyl-imidazo[4,5-b]pyridin-2-amines, 4-indazolyl-N-phenylpyrimidin-2-amines and N-phenyl-4-pyrazolo[3,4-b]pyridin-pyrimidin-2-amines have been synthesized. Their anti-proliferative activities were tested in HCT-116 human colon carcinoma and MCF-7 breast carcinoma cell lines. Many exhibited potent anti-proliferative and CDK9 inhibitory activities. A lead compound 18b demonstrated the ability to reduce the level of Mcl-1 anti-apoptotic protein, to activate caspase 3/7 and induce cancer cell apoptosis. (C) 2012 Elsevier Masson SAS. All rights reserved.