3-(2,4-dimethyl-1H-pyrrol-3-yl)-1-(4-methylpiperazin-1-yl)propan-1-one | 515138-77-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 英文名称: 3-(2,4-dimethyl-1H-pyrrol-3-yl)-1-(4-methylpiperazin-1-yl)propan-1-one
• CAS: 515138-77-9
• 化学式: C₁₄H₂₃N₃O
• 分子量: 249.356
• InChiKey: ZAPGWPFCFNZWAX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  39.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-(2,4-dimethyl-1H-pyrrol-3-yl)-1-(4-methylpiperazin-1-yl)propan-1-one 在 lithium aluminium tetrahydride 、 三氯氧磷 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 5.0h， 生成 3,5-dimethyl-4-[3-(4-methylpiperazin-1-yl)propyl]-1H-pyrrole-2-carbaldehyde
  参考文献：
  名称：

  Discovery of 5-[5-Fluoro-2-oxo-1,2- dihydroindol-(3Z)-ylidenemethyl]-2,4- dimethyl-1H-pyrrole-3-carboxylic Acid (2-Diethylaminoethyl)amide, a Novel Tyrosine Kinase Inhibitor Targeting Vascular Endothelial and Platelet-Derived Growth Factor Receptor Tyrosine Kinase

  摘要：

  To improve the antitumor properties and optimize the pharmaceutical properties including solubility and protein binding of indolin-2-ones, a number of different basic and weakly basic analogues were designed and synthesized. 5-[5-Fluoro-2-oxo-1,2-dihydroindol-(3Z)-ylidenemethyl]-2,4-dimethyl- 1H-pyrrole-3-carboxylic acid (2-diethylaminoethyl)amide (12b or SU11248) has been found to show the best overall profile in terms of potency for the VEGF-R2 and PDGF-Rbeta tyrosine kinase at biochemical and cellular levels, solubility, protein binding, and bioavailability. 12b is currently in phase I clinical trials for the treatment of cancers.

  DOI：

  10.1021/jm0204183
• 作为产物：
  描述：

  N-甲基哌嗪 、 2,4-二甲基3-吡咯丙 酸 在 N,N'-羰基二咪唑 作用下， 以 二氯甲烷 为溶剂， 以96%的产率得到3-(2,4-dimethyl-1H-pyrrol-3-yl)-1-(4-methylpiperazin-1-yl)propan-1-one
  参考文献：
  名称：

  Discovery of 5-[5-Fluoro-2-oxo-1,2- dihydroindol-(3Z)-ylidenemethyl]-2,4- dimethyl-1H-pyrrole-3-carboxylic Acid (2-Diethylaminoethyl)amide, a Novel Tyrosine Kinase Inhibitor Targeting Vascular Endothelial and Platelet-Derived Growth Factor Receptor Tyrosine Kinase

  摘要：

  To improve the antitumor properties and optimize the pharmaceutical properties including solubility and protein binding of indolin-2-ones, a number of different basic and weakly basic analogues were designed and synthesized. 5-[5-Fluoro-2-oxo-1,2-dihydroindol-(3Z)-ylidenemethyl]-2,4-dimethyl- 1H-pyrrole-3-carboxylic acid (2-diethylaminoethyl)amide (12b or SU11248) has been found to show the best overall profile in terms of potency for the VEGF-R2 and PDGF-Rbeta tyrosine kinase at biochemical and cellular levels, solubility, protein binding, and bioavailability. 12b is currently in phase I clinical trials for the treatment of cancers.

  DOI：

  10.1021/jm0204183

文献信息

• Discovery of 5-[5-Fluoro-2-oxo-1,2- dihydroindol-(3<i>Z</i>)-ylidenemethyl]-2,4- dimethyl-1<i>H</i>-pyrrole-3-carboxylic Acid (2-Diethylaminoethyl)amide, a Novel Tyrosine Kinase Inhibitor Targeting Vascular Endothelial and Platelet-Derived Growth Factor Receptor Tyrosine Kinase
  作者：Li Sun、Chris Liang、Sheri Shirazian、Yong Zhou、Todd Miller、Jean Cui、Juri Y. Fukuda、Ji-Yu Chu、Asaad Nematalla、Xueyan Wang、Hui Chen、Anand Sistla、Tony C. Luu、Flora Tang、James Wei、Cho Tang

  DOI：10.1021/jm0204183

  日期：2003.3.1

  To improve the antitumor properties and optimize the pharmaceutical properties including solubility and protein binding of indolin-2-ones, a number of different basic and weakly basic analogues were designed and synthesized. 5-[5-Fluoro-2-oxo-1,2-dihydroindol-(3Z)-ylidenemethyl]-2,4-dimethyl- 1H-pyrrole-3-carboxylic acid (2-diethylaminoethyl)amide (12b or SU11248) has been found to show the best overall profile in terms of potency for the VEGF-R2 and PDGF-Rbeta tyrosine kinase at biochemical and cellular levels, solubility, protein binding, and bioavailability. 12b is currently in phase I clinical trials for the treatment of cancers.