4-(3-Aminooxalyl-1-benzyl-2-methyl-1H-indol-5-yl)-4-oxo-butyric acid ethyl ester | 185501-28-4

• 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: 4-(3-Aminooxalyl-1-benzyl-2-methyl-1H-indol-5-yl)-4-oxo-butyric acid ethyl ester
• 英文别名: Ethyl 4-(1-benzyl-2-methyl-3-oxamoylindol-5-yl)-4-oxobutanoate
• CAS: 185501-28-4
• 化学式: C₂₄H₂₄N₂O₅
• 分子量: 420.465
• InChiKey: CJHVMDGZNTZADR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  31
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  109
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-(3-Aminooxalyl-1-benzyl-2-methyl-1H-indol-5-yl)-4-oxo-butyric acid ethyl ester 在 三乙基硅烷 、 sodium hydroxide 、 三氟乙酸 作用下， 以 乙醇 、 1,2-二氯乙烷 为溶剂， 反应 38.0h， 生成 4-(1-Benzyl-3-carbamoylmethyl-2-methyl-1H-indol-5-yl)-butyric 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：

  1-(2-甲基-2,3-二氢-吲哚-1-基)-乙酮 在 三氯化铝 、 硫酸 、 氨 、 potassium carbonate 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 1,4-二氧六环 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 23.0h， 生成 4-(3-Aminooxalyl-1-benzyl-2-methyl-1H-indol-5-yl)-4-oxo-butyric 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