5-([1,1'-biphenyl]-3-yl)-4-bromo-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrrole-2-carbaldehyde | 1191422-83-9

• 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: 5-([1,1'-biphenyl]-3-yl)-4-bromo-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrrole-2-carbaldehyde
• CAS: 1191422-83-9
• 化学式: C₂₃H₂₆BrNO₂Si
• 分子量: 456.454
• InChiKey: GCZXPZZEWSIJQM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.71
• 重原子数：
  28.0
• 可旋转键数：
  8.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  31.23
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  2-(N-t-butyoxycarbonylamino)histamine 、 5-([1,1'-biphenyl]-3-yl)-4-bromo-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrrole-2-carbaldehyde 生成
  参考文献：
  名称：

  Synthesis of novel ageladine A analogs showing more potent matrix metalloproteinase (MMP)-12 inhibitory activity than the natural product

  摘要：

  By employing a previously established synthetic scheme, the synthesis described in the title was carried out in order to explore the substituent effects in the pyrrole ring of ageladine A on MMP-12 inhibitory activity. It became evident that a halogen atom (Br or Cl) at the 2-position and an additional bromine atom at the 4-position are highly effective for improving the inhibitory activity. These studies led us to discover three novel ageladine A analogs (4a. c, o) showing more potent MMP-12 inhibitory activity than the natural product. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.07.099
• 作为产物：
  描述：

  4,5-dibromo-1-(2-trimethylsilylethoxymethyl)pyrrol-2-carbaldehyde 、 3-联苯硼酸 在 palladium diacetate 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 5-([1,1'-biphenyl]-3-yl)-4-bromo-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrrole-2-carbaldehyde
  参考文献：
  名称：

  Synthesis of novel ageladine A analogs showing more potent matrix metalloproteinase (MMP)-12 inhibitory activity than the natural product

  摘要：

  By employing a previously established synthetic scheme, the synthesis described in the title was carried out in order to explore the substituent effects in the pyrrole ring of ageladine A on MMP-12 inhibitory activity. It became evident that a halogen atom (Br or Cl) at the 2-position and an additional bromine atom at the 4-position are highly effective for improving the inhibitory activity. These studies led us to discover three novel ageladine A analogs (4a. c, o) showing more potent MMP-12 inhibitory activity than the natural product. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.07.099