4-[[3-(2-amino-1,2-dioxoethyl)-1-(phenylmethyl)-1H-indol-5-yl]oxy]butanoic acid ethyl ester | 172733-35-6

• 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-[[3-(2-amino-1,2-dioxoethyl)-1-(phenylmethyl)-1H-indol-5-yl]oxy]butanoic acid ethyl ester
• 英文别名: Ethyl 4-(1-benzyl-3-oxamoylindol-5-yl)oxybutanoate
• CAS: 172733-35-6
• 化学式: C₂₃H₂₄N₂O₅
• 分子量: 408.454
• InChiKey: CROZTSRXFXKQCG-UHFFFAOYSA-N

物化性质

• 熔点：
  168-170 °C
• 沸点：
  639.2±65.0 °C(Predicted)
• 密度：
  1.24±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  30
• 可旋转键数：
  11
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  101
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-[[3-(2-amino-1,2-dioxoethyl)-1-(phenylmethyl)-1H-indol-5-yl]oxy]butanoic acid ethyl ester 在 盐酸 作用下， 以 四氢呋喃 为溶剂， 以45%的产率得到4-[[3-(2-amino-1,2-dioxoethyl)-1-(phenylmethyl)-1H-indol-5-yl]oxy]butanoic acid
  参考文献：
  名称：

  1H-indole-3-glyoxylamide SPLA.sub.2 inhibitors

  摘要：

  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。

  公开号：

  US05654326A1
• 作为产物：
  描述：

  1-苄基-5-甲氧基吲哚 在 氨 、 三溴化硼 、 sodium hydride 作用下， 以 二氯甲烷 为溶剂， 反应 23.0h， 生成 4-[[3-(2-amino-1,2-dioxoethyl)-1-(phenylmethyl)-1H-indol-5-yl]oxy]butanoic acid ethyl 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。
• 1H-indole-3-glyoxylamide spla2 inhibitors
  申请人：ELI LILLY AND COMPANY

  公开号：EP1081135A2

  公开（公告）日：2001-03-07

  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.

  本研究公开了一类新型 1H-吲哚-3-乙二酰氨基化合物，以及此类吲哚化合物在抑制 sPLA2 介导的脂肪酸释放以治疗脓毒性休克等疾病方面的用途。
• [[3-(2-amino-1,2-dioxoethyl)-2-ethyl-1-(phenylmethyl)-11H-indol-4-yl]oxy]acetic acid methyl ester as sPLA2 inhibitor
  申请人：ELI LILLY AND COMPANY

  公开号：EP1950200A1

  公开（公告）日：2008-07-30

  The compound [[3-(2-amino-1,2-dioxoethyl)-2-ethyl-1-(phenylmethyl)-1H-indol-4- yl]oxy]acetic acid methyl ester is disclosed together with the use of indole compound for inhibiting sPLA2 mediated release of fatty acids for treatment of conditions such as septic shock.

  The compound [[3-(2-amino-1,2-dioxoethyl)-2-ethyl-1-(phenylmethyl)-1H-indol-4- yl]氧基]乙酸甲酯，以及吲哚化合物用于抑制 sPLA2 介导的脂肪酸释放以治疗脓毒性休克等疾病的用途。
• [[3-(2-amino-1,2-dioxoethyl)-2-ethyl-1-(phenylmethyl)-11H-indol-4-yl]oxy]acetic acid (acyloxy)alkyl or ((alkoxycarbonyl)oxy)alkyl ester as SPLA2 inhibitor
  申请人：Eli Lilly and Company

  公开号：EP2341045A1

  公开（公告）日：2011-07-06

  The compounds [[3-(2-amino-1,2-diooethyl)-2-ethyl-1-(phenylmethyl)-1H-indol-4-yl]oxy]acetic acid (acyloxy) alkyl or ((alkoxycarbonyl)oxy)alkyl ester are disclosed together with the use of the indole compound for inhibiting sPLA2 mediated release of fatty acids for treatment of conditions such as septic shock.

  公开了[[3-(2-氨基-1,2-二氧乙基)-2-乙基-1-(苯基甲基)-1H-吲哚-4-基]氧基]乙酸（酰氧基）烷基或（（烷氧羰基）氧基）烷基酯化合物，以及吲哚化合物用于抑制 sPLA2 介导的脂肪酸释放以治疗脓毒性休克等疾病的用途。
• 1H-Indole-3-glyoxylamide sPLA2 inhibitors
  申请人：ELI LILLY AND COMPANY

  公开号：EP0675110B1

  公开（公告）日：2002-07-10