2-acetyl-4-(dimethylethoxycarbonyl)aminomethylpyrrole | 850716-39-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-acetyl-4-(dimethylethoxycarbonyl)aminomethylpyrrole
• 英文别名: tert-butyl N-[(5-acetyl-1H-pyrrol-3-yl)methyl]carbamate
• CAS: 850716-39-1
• 化学式: C₁₂H₁₈N₂O₃
• 分子量: 238.287
• InChiKey: CMKDNPIXPKZARN-UHFFFAOYSA-N

物化性质

• 沸点：
  417.0±40.0 °C(Predicted)
• 密度：
  1.132±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  71.2
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-acetyl-4-(dimethylethoxycarbonyl)aminomethylpyrrole 在 哌啶 、 吡啶 、 盐酸 、 四氯化锡 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 乙醇 、 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 生成 [(3Z)-3-{1-[4-(aminomethyl)-1H-pyrrol-2-yl]ethylidene}-2-oxo-2,3-dihydro-1H-indol-5-yl]urea
  参考文献：
  名称：

  Indolinone based phosphoinositide-dependent kinase-1 (PDK1) inhibitors. Part 2: Optimization of BX-517

  摘要：

  Based on the lead compound BX-517, a series of C-4 ' substituted indolinones have been synthesized and evaluated for PDK1 inhibition. Modification at C-4 ' of the pyrrole afforded potent compounds (7b and 7d) with improved solubility and ADME properties. In this letter, we describe the synthesis, selectivity profile, and pharmacokinetic data of selected compounds. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.05.060
• 作为产物：
  描述：

  二碳酸二叔丁酯 、 2-acetylpyrrole-4-carbonitrile 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 以73%的产率得到2-acetyl-4-(dimethylethoxycarbonyl)aminomethylpyrrole
  参考文献：
  名称：

  Indolinone based phosphoinositide-dependent kinase-1 (PDK1) inhibitors. Part 2: Optimization of BX-517

  摘要：

  Based on the lead compound BX-517, a series of C-4 ' substituted indolinones have been synthesized and evaluated for PDK1 inhibition. Modification at C-4 ' of the pyrrole afforded potent compounds (7b and 7d) with improved solubility and ADME properties. In this letter, we describe the synthesis, selectivity profile, and pharmacokinetic data of selected compounds. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.05.060

文献信息

• Indolinone derivatives and their use in treating disease-states such as cancer
  申请人：Arnaiz Damian

  公开号：US20050090541A1

  公开（公告）日：2005-04-28

  Indolinone derivatives, such as compounds of the formula (I): wherein A, m, n, R 1 , R 2 , R 3 , R 5 and R 6 are described herein, are disclosed herein as being useful in treating mammal having disease-states alleviated by the inhibition of PDK-1 activity.

  Indolinone衍生物，例如公式（I）中的化合物：其中A，m，n，R1，R2，R3，R5和R6如本文所述，据本文披露，可用于治疗通过抑制PDK-1活性缓解疾病状态的哺乳动物。
• US7105563B2
  申请人：——

  公开号：US7105563B2

  公开（公告）日：2006-09-12
• Indolinone based phosphoinositide-dependent kinase-1 (PDK1) inhibitors. Part 2: Optimization of BX-517
  作者：Imadul Islam、Greg Brown、Judi Bryant、Paul Hrvatin、Monica J. Kochanny、Gary B. Phillips、Shendong Yuan、Marc Adler、Marc Whitlow、Dao Lentz、Mark A. Polokoff、James Wu、Jun Shen、Janette Walters、Elena Ho、Babu Subramanyam、Daguang Zhu、Richard I. Feldman、Damian O. Arnaiz

  DOI：10.1016/j.bmcl.2007.05.060

  日期：2007.7

  Based on the lead compound BX-517, a series of C-4 ' substituted indolinones have been synthesized and evaluated for PDK1 inhibition. Modification at C-4 ' of the pyrrole afforded potent compounds (7b and 7d) with improved solubility and ADME properties. In this letter, we describe the synthesis, selectivity profile, and pharmacokinetic data of selected compounds. (C) 2007 Elsevier Ltd. All rights reserved.