((2-methyl-1-(phenylmethyl)-1H-indol-4-yl)oxy)acetic acid methyl ester | 172732-79-5

• 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: ((2-methyl-1-(phenylmethyl)-1H-indol-4-yl)oxy)acetic acid methyl ester
• 英文别名: [[2-methyl-1-(phenylmethyl)-1H-indol-4-yl]oxy]acetic acid methyl ester；(1-benzyl-2-methyl-1H-indol-4-yloxy)-acetic acid methyl ester；methyl 2-(1-benzyl-2-methylindol-4-yl)oxyacetate
• CAS: 172732-79-5
• 化学式: C₁₉H₁₉NO₃
• 分子量: 309.365
• InChiKey: LSPWMIBSUHRLAP-UHFFFAOYSA-N

物化性质

• 熔点：
  140-145 °C
• 沸点：
  482.5±40.0 °C(Predicted)
• 密度：
  1.13±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  40.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ((2-methyl-1-(phenylmethyl)-1H-indol-4-yl)oxy)acetic acid methyl ester 在 氨 作用下， 以 二氯甲烷 为溶剂， 反应 1.33h， 生成 ((3-(2-Amino-1,2-dioxoethyl)-2-methyl-1-(phenylmethyl)-1H-indol-4-yl)oxy)-acetic acid methyl ester
  参考文献：
  名称：

  Indole Inhibitors of Human Nonpancreatic Secretory Phospholipase A₂. 3. Indole-3-glyoxamides

  摘要：

  The preceding papers of this series detail the development of functionalized indole-3-acetamides as inhibitors of hnps-PLA(2). We describe here the extension of the structure-activity relationship to include a series of indole-3-glyoxamide derivatives. Functionalized indole-3-glyoxamides with an acidic substituent appended to the 4- or 5-position of the indole ring were prepared and tested as inhibitors of hnps-PLA(2). It was found that the indole-3-glyoxamides with a 4-oxyacetic acid substituent had optimal inhibitory activity. These inhibitors exhibited an improvement in potency over the best of the indole-3-acetamides, and LY315920 (6m) was selected for evaluation clinically as an hnps-PLA(2) inhibitor.

  DOI：

  10.1021/jm960487f
• 作为产物：
  描述：

  4-Methoxy-2-methyl-1-(phenylmethyl)-1H-indole 在 三溴化硼 、 sodium hydride 作用下， 以 二氯甲烷 为溶剂， 反应 21.67h， 生成 ((2-methyl-1-(phenylmethyl)-1H-indol-4-yl)oxy)acetic acid methyl ester
  参考文献：
  名称：

  Indole Inhibitors of Human Nonpancreatic Secretory Phospholipase A₂. 3. Indole-3-glyoxamides

  摘要：

  The preceding papers of this series detail the development of functionalized indole-3-acetamides as inhibitors of hnps-PLA(2). We describe here the extension of the structure-activity relationship to include a series of indole-3-glyoxamide derivatives. Functionalized indole-3-glyoxamides with an acidic substituent appended to the 4- or 5-position of the indole ring were prepared and tested as inhibitors of hnps-PLA(2). It was found that the indole-3-glyoxamides with a 4-oxyacetic acid substituent had optimal inhibitory activity. These inhibitors exhibited an improvement in potency over the best of the indole-3-acetamides, and LY315920 (6m) was selected for evaluation clinically as an hnps-PLA(2) inhibitor.

  DOI：

  10.1021/jm960487f

文献信息

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

  公开号：US05654326A1

  公开（公告）日：1997-08-05

  A class of novel 1H-indole-3-glyoxylamides is disclosed together with the use of such indole compounds for inhibiting sPLA.sub.2 mediated release of fatty acids for treatment of conditions such as septic shock.

  一种新型的1H-吲哚-3-甘氧酰胺类化合物被揭示，以及利用这类吲哚化合物抑制sPLA.sub.2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。
• Method for treating sepsis
  申请人：——

  公开号：US20040110825A1

  公开（公告）日：2004-06-10

  A novel method of treating and/or preventing sepsis.

  一种治疗和/或预防败血症的新方法。
• sPLA2 inhibitor ester
  申请人：Eli Lilly and Company

  公开号：US06274578B1

  公开（公告）日：2001-08-14

  The compound, ((3(2-amino-1,2-dioxoethyl)-2-methyl-1-(phenylmethyl)-1H-indol-4-yl)oxy)acetic acid N-morpholino ester, is disclosed together with its use as a highly bioavailable indole sPLA2 inhibitor compound.

  这种化合物，((3(2-氨基-1,2-二氧乙基)-2-甲基-1-(苯甲基)-1H-吲哚-4-基氧)乙酸N-吗啉酯)，以及其作为高生物利用度吲哚sPLA2抑制剂化合物的用途被披露。
• 1H-indole-3-glyoxylamide sPLA.sub.2 inhibitors
  申请人：Eli Lilly and Company

  公开号：US05733923A1

  公开（公告）日：1998-03-31

  A class of novel 1H-indole-3-glyoxylamides is disclosed together with the use of such indole compounds for inhibiting sPLA.sub.2 mediated release of fatty acids for treatment of conditions such as septic shock.

  一种新型的1H-吲哚-3-甘氧酰胺类化合物被披露，以及使用这些吲哚化合物抑制sPLA.sub.2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-glyoxylamide sPLA2 inhibitors
  申请人：Eli Lilly and Company

  公开号：US06433001B1

  公开（公告）日：2002-08-13

  A class of novel 1H-indole-3-glyoxylamides 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.

  一类新型的1H-吲哚-3-乙酰胺基甲酸酰胺被揭示，以及使用这种吲哚化合物来抑制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。