4-(benzyloxy)-2-ethyl-6-methyl-1H-indole | 889674-98-0

• 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: 4-(benzyloxy)-2-ethyl-6-methyl-1H-indole
• 英文别名: 2-ethyl-6-methyl-4-phenylmethoxy-1H-indole
• CAS: 889674-98-0
• 化学式: C₁₈H₁₉NO
• 分子量: 265.355
• InChiKey: VKRFGUWKDCHECY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  25
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  4-(benzyloxy)-2-ethyl-6-methyl-1H-indole 在 palladium on activated charcoal 氢气 、 sodium hydride 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 20.0 ℃ 、275.79 kPa 条件下， 反应 4.66h， 生成 tert-butyl 2-(1-benzyl-2-ethyl-6-methyl-1H-indol-4-yloxy)acetate
  参考文献：
  名称：

  The First Potent Inhibitor of Mammalian Group X Secreted Phospholipase A₂:  Elucidation of Sites for Enhanced Binding

  摘要：

  Using the X-ray structure of human group X secreted phospholipase A(2) (hGX), we carried out structure-based design of indole-based inhibitors and prepared the compounds using a new synthetic route. The most potent compound inhibited hGX and the mouse orthologue with an IC50 of 75 nM. This compound is the most potent hGX inhibitor reported to date and was also found to inhibit a subset of the other mouse and human sPLA(2)s.

  DOI：

  10.1021/jm060136t
• 作为产物：
  描述：

  4-(benzyloxy)-6-methyl-1-(phenylsulfonyl)-1H-indole 在 sodium tetrahydroborate 、 lithium aluminium tetrahydride 、 正丁基锂 、 三氟乙酸 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 38.0h， 生成 4-(benzyloxy)-2-ethyl-6-methyl-1H-indole
  参考文献：
  名称：

  The First Potent Inhibitor of Mammalian Group X Secreted Phospholipase A₂:  Elucidation of Sites for Enhanced Binding

  摘要：

  Using the X-ray structure of human group X secreted phospholipase A(2) (hGX), we carried out structure-based design of indole-based inhibitors and prepared the compounds using a new synthetic route. The most potent compound inhibited hGX and the mouse orthologue with an IC50 of 75 nM. This compound is the most potent hGX inhibitor reported to date and was also found to inhibit a subset of the other mouse and human sPLA(2)s.

  DOI：

  10.1021/jm060136t

文献信息

• The First Potent Inhibitor of Mammalian Group X Secreted Phospholipase A₂:  Elucidation of Sites for Enhanced Binding
  作者：Brian P. Smart、Rob C. Oslund、Laura A. Walsh、Michael H. Gelb

  DOI：10.1021/jm060136t

  日期：2006.5.1

  Using the X-ray structure of human group X secreted phospholipase A(2) (hGX), we carried out structure-based design of indole-based inhibitors and prepared the compounds using a new synthetic route. The most potent compound inhibited hGX and the mouse orthologue with an IC50 of 75 nM. This compound is the most potent hGX inhibitor reported to date and was also found to inhibit a subset of the other mouse and human sPLA(2)s.