dibenzyl 1-[3-(4-octylphenoxy)-2-oxopropyl]indole-3,5-dicarboxylate | 888319-97-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: dibenzyl 1-[3-(4-octylphenoxy)-2-oxopropyl]indole-3,5-dicarboxylate
• CAS: 888319-97-9
• 化学式: C₄₁H₄₃NO₆
• 分子量: 645.796
• InChiKey: CHQUFXBLZJIVER-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.3
• 重原子数：
  48
• 可旋转键数：
  20
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  83.8
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  dibenzyl 1-[3-(4-octylphenoxy)-2-oxopropyl]indole-3,5-dicarboxylate 在 palladium on activated charcoal 氢气 作用下， 以 四氢呋喃 为溶剂， 反应 5.0h， 以56%的产率得到1-[3-(4-Octylphenoxy)-2-oxopropyl]indole-3,5-dicarboxylic acid
  参考文献：
  名称：

  Design and Synthesis of 1-Indol-1-yl-propan-2-ones as Inhibitors of Human Cytosolic Phospholipase A₂α

  摘要：

  The synthesis and structure-activity relationship study of a series of 1-indol-1-yl-3-phenoxypropan-2-one inhibitors of cytosolic phospholipase A(2)alpha (cPLA(2)alpha) are described. The compounds were evaluated in a vesicle assay with isolated cPLA(2)alpha and in cellular assays with intact human platelets. Systematic variation led to 3-methylhydrogen 1-[3-(4-decyloxyphenoxy)-2-oxopropyl]indole-3,5-dicarboxylate (57), which revealed the highest activity against the isolated enzyme. With an IC50 value of 4.3 nM in this assay, it is one of the most potent in vitro cPLA(2)alpha inhibitors known today.

  DOI：

  10.1021/jm051243a
• 作为产物：
  描述：

  dimethyl 1H-indole-3,5-dicarboxylate 在 乙酸酐 、 potassium hydride 、 sodium hydride 、 二甲基亚砜 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 45.25h， 生成 dibenzyl 1-[3-(4-octylphenoxy)-2-oxopropyl]indole-3,5-dicarboxylate
  参考文献：
  名称：

  Design and Synthesis of 1-Indol-1-yl-propan-2-ones as Inhibitors of Human Cytosolic Phospholipase A₂α

  摘要：

  The synthesis and structure-activity relationship study of a series of 1-indol-1-yl-3-phenoxypropan-2-one inhibitors of cytosolic phospholipase A(2)alpha (cPLA(2)alpha) are described. The compounds were evaluated in a vesicle assay with isolated cPLA(2)alpha and in cellular assays with intact human platelets. Systematic variation led to 3-methylhydrogen 1-[3-(4-decyloxyphenoxy)-2-oxopropyl]indole-3,5-dicarboxylate (57), which revealed the highest activity against the isolated enzyme. With an IC50 value of 4.3 nM in this assay, it is one of the most potent in vitro cPLA(2)alpha inhibitors known today.

  DOI：

  10.1021/jm051243a

文献信息

• Design and Synthesis of 1-Indol-1-yl-propan-2-ones as Inhibitors of Human Cytosolic Phospholipase A₂α
  作者：Joachim Ludwig、Stefanie Bovens、Carsten Brauch、Alwine Schulze Elfringhoff、Matthias Lehr

  DOI：10.1021/jm051243a

  日期：2006.4.1

  The synthesis and structure-activity relationship study of a series of 1-indol-1-yl-3-phenoxypropan-2-one inhibitors of cytosolic phospholipase A(2)alpha (cPLA(2)alpha) are described. The compounds were evaluated in a vesicle assay with isolated cPLA(2)alpha and in cellular assays with intact human platelets. Systematic variation led to 3-methylhydrogen 1-[3-(4-decyloxyphenoxy)-2-oxopropyl]indole-3,5-dicarboxylate (57), which revealed the highest activity against the isolated enzyme. With an IC50 value of 4.3 nM in this assay, it is one of the most potent in vitro cPLA(2)alpha inhibitors known today.