[3-[[3-(2-ethoxy-2-oxoethyl)-1-(phenylmethyl)-1H-indol-5-yl]oxy]propyl]phosphonic acid dimethyl ester | 164082-99-9

• 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: [3-[[3-(2-ethoxy-2-oxoethyl)-1-(phenylmethyl)-1H-indol-5-yl]oxy]propyl]phosphonic acid dimethyl ester
• 英文别名: ethyl 2-[1-benzyl-5-(3-dimethoxyphosphorylpropoxy)indol-3-yl]acetate
• CAS: 164082-99-9
• 化学式: C₂₄H₃₀NO₆P
• 分子量: 459.479
• InChiKey: AJKRYKQFNCOTPZ-UHFFFAOYSA-N

物化性质

• 沸点：
  622.6±55.0 °C(Predicted)
• 密度：
  1.20±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  32
• 可旋转键数：
  13
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  76
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  [3-[[3-(2-ethoxy-2-oxoethyl)-1-(phenylmethyl)-1H-indol-5-yl]oxy]propyl]phosphonic acid dimethyl ester 在 氯(甲基)铝酰胺 作用下， 以 甲苯 、 苯 为溶剂， 反应 1.25h， 以80%的产率得到[3-[[3-(2-amino-2-oxoethyl)-1-(phenylmethyl)-1H-indol-5-yl]oxy]propyl]phosphonic acid dimethyl ester
  参考文献：
  名称：

  Indole Inhibitors of Human Nonpancreatic Secretory Phospholipase A₂. 2. Indole-3-acetamides with Additional Functionality

  摘要：

  As reported in our previous paper, a series of indole-3-acetamides which possessed potency and selectivity as inhibitors of human nonpancreatic secretory phospholipase A(2)(hnps-PLA(2)) was developed. The design of these compounds was based on information derived from x-ray crystal structures determined for complexes between the enzyme and its inhibitors. We describe here the further implementation of this structure-based design strategy and continued SAR development to produce indole-3-acetamides with additional functionalities which provide increased interaction with important residues within the enzyme active site. These efforts led to inhibitors with substantially enhanced potency and selectivity.

  DOI：

  10.1021/jm960486n
• 作为产物：
  描述：

  dimethyl (3-bromopropyl)phosphonate 、 Ethyl 2-(1-benzyl-5-hydroxyindol-3-yl)acetate 在 sodium hydride 作用下， 生成 [3-[[3-(2-ethoxy-2-oxoethyl)-1-(phenylmethyl)-1H-indol-5-yl]oxy]propyl]phosphonic acid dimethyl ester
  参考文献：
  名称：

  Indole Inhibitors of Human Nonpancreatic Secretory Phospholipase A₂. 2. Indole-3-acetamides with Additional Functionality

  摘要：

  As reported in our previous paper, a series of indole-3-acetamides which possessed potency and selectivity as inhibitors of human nonpancreatic secretory phospholipase A(2)(hnps-PLA(2)) was developed. The design of these compounds was based on information derived from x-ray crystal structures determined for complexes between the enzyme and its inhibitors. We describe here the further implementation of this structure-based design strategy and continued SAR development to produce indole-3-acetamides with additional functionalities which provide increased interaction with important residues within the enzyme active site. These efforts led to inhibitors with substantially enhanced potency and selectivity.

  DOI：

  10.1021/jm960486n

文献信息

• 1H-indole-3-acetamide sPLA.sub.2 inhibitors
  申请人：Eli Lilly and Company

  公开号：US05684034A1

  公开（公告）日：1997-11-04

  A class of novel 1-indole-3-acetamides represented by the formula; ##STR1## is disclosed together with the use of such indole compounds for inhibiting sPLA.sub.2 mediated release of fatty acids.

  一类由以下式表示的新型1-吲哚-3-乙酰胺类化合物被揭示，同时还公开了利用这类吲哚化合物抑制sPLA.sub.2介导的脂肪酸释放的用途。
• 1H-indole-3-acetamide sPLA2 inhibitors
  申请人：Eli Lilly and Company

  公开号：US06252084B1

  公开（公告）日：2001-06-26

  A class of novel 1H-indole-3-acetamides is disclosed together with the use of such indole compounds for inhibiting sPLA2 mediated release of fatty acids for treatment of conditions such as septic shock.

  一类新型1H-吲哚-3-乙酰胺被揭示，以及使用这些吲哚化合物抑制sPLA2介导的脂肪酸释放，用于治疗诸如感染性休克等疾病的方法。
• 1H-indole-3-acetamide derivatives as sPLA2 inhibitors
  申请人：ELI LILLY AND COMPANY

  公开号：EP0620215B1

  公开（公告）日：1999-08-18
• US6252084B1
  申请人：——

  公开号：US6252084B1

  公开（公告）日：2001-06-26