ethyl [4-[3-(amidomethyl)-2-ethyl-1-(phenylmethyl)-indol-5-yl]oxy]butanoate | 164083-79-8

• 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: ethyl [4-[3-(amidomethyl)-2-ethyl-1-(phenylmethyl)-indol-5-yl]oxy]butanoate
• 英文别名: 4-(1-Benzyl-3-carbamoylmethyl-2-ethyl-1H-indol-5-yloxy)-butyric acid ethyl ester；ethyl 4-[3-(2-amino-2-oxoethyl)-1-benzyl-2-ethylindol-5-yl]oxybutanoate
• CAS: 164083-79-8
• 化学式: C₂₅H₃₀N₂O₄
• 分子量: 422.524
• InChiKey: HEYJAXJJAKTSOP-UHFFFAOYSA-N

物化性质

• 沸点：
  660.1±55.0 °C(Predicted)
• 密度：
  1.16±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  31
• 可旋转键数：
  12
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  83.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl [4-[3-(amidomethyl)-2-ethyl-1-(phenylmethyl)-indol-5-yl]oxy]butanoate 在 肼 作用下， 以 乙醇 为溶剂， 反应 20.0h， 生成 2-ethyl-5-(4-hydrazino-4-oxobutoxy)-1-(phenylmethyl)-1H-indole-3-acetamide
  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：

  3-(cyanomethyl)-2-ethyl-1-(phenylmethyl)-5-methoxyindole 在 氢氧化钾 、 三溴化硼 、 sodium hydride 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 、 叔丁醇 为溶剂， 反应 6.0h， 生成 ethyl [4-[3-(amidomethyl)-2-ethyl-1-(phenylmethyl)-indol-5-yl]oxy]butanoate
  参考文献：
  名称：

  Synthesis of indomethacin analogues for evaluation as modulators of MRP activity

  摘要：

  Synthesis of a range of indomethacin analogues, required for investigation in combination toxicity assays, bearing both N-benzyl and N-benzoyl groups, is described. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(00)00292-3

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.

  本发明揭示了一类由以下式子表示的新型1-吲哚-3-乙酰胺：##STR1## 以及使用这些吲哚化合物来抑制sPLA.sub.2介导的脂肪酸释放的方法。
• 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。
• Indole Inhibitors of Human Nonpancreatic Secretory Phospholipase A₂. 2. Indole-3-acetamides with Additional Functionality
  作者：Robert D. Dillard、Nicholas J. Bach、Susan E. Draheim、Dennis R. Berry、Donald G. Carlson、Nickolay Y. Chirgadze、David K. Clawson、Lawrence W. Hartley、Lea M. Johnson、Noel D. Jones、Emma R. McKinney、Edward D. Mihelich、Jennifer L. Olkowski、Richard W. Schevitz、Amy C. Smith、David W. Snyder、Cynthia D. Sommers、Jean-Pierre Wery

  DOI：10.1021/jm960486n

  日期：1996.1.1

  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.
• Synthesis of indomethacin analogues for evaluation as modulators of MRP activity
  作者：Anita R. Maguire、Stephen J. Plunkett、Sébastien Papot、Martin Clynes、Robert O'Connor、Samantha Touhey

  DOI：10.1016/s0968-0896(00)00292-3

  日期：2001.3

  Synthesis of a range of indomethacin analogues, required for investigation in combination toxicity assays, bearing both N-benzyl and N-benzoyl groups, is described. (C) 2001 Elsevier Science Ltd. All rights reserved.