3-(1-Benzyl-3-carbamoylmethyl-2-methyl-1H-indol-5-yloxy)-benzoic acid ethyl ester | 185500-96-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-(1-Benzyl-3-carbamoylmethyl-2-methyl-1H-indol-5-yloxy)-benzoic acid ethyl ester
• 英文别名: Ethyl 3-[3-(2-amino-2-oxoethyl)-1-benzyl-2-methylindol-5-yl]oxybenzoate
• CAS: 185500-96-3
• 化学式: C₂₇H₂₆N₂O₄
• 分子量: 442.514
• InChiKey: QPXKOLVBLDKYKD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  33
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.19
• 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：

  3-(1-Benzyl-3-carbamoylmethyl-2-methyl-1H-indol-5-yloxy)-benzoic acid ethyl ester 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 1.5h， 生成 3-(1-Benzyl-3-carbamoylmethyl-2-methyl-1H-indol-5-yloxy)-benzoic acid
  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-(amidomethyl)-2-methyl-1-(phenylmethyl)-5-methoxyindole 在 吡啶 、 三溴化硼 、 sodium hydride 、 copper(I) bromide 作用下， 以 二氯甲烷 为溶剂， 反应 16.92h， 生成 3-(1-Benzyl-3-carbamoylmethyl-2-methyl-1H-indol-5-yloxy)-benzoic acid ethyl 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