3-[1-Benzyl-3-(carbamoyl-hydroxy-methyl)-2-ethyl-1H-indol-5-ylsulfanyl]-propionic acid tert-butyl ester | 1026554-90-4

• 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: 3-[1-Benzyl-3-(carbamoyl-hydroxy-methyl)-2-ethyl-1H-indol-5-ylsulfanyl]-propionic acid tert-butyl ester
• 英文别名: Tert-butyl 3-[3-(2-amino-1-hydroxy-2-oxoethyl)-1-benzyl-2-ethylindol-5-yl]sulfanylpropanoate
• CAS: 1026554-90-4
• 化学式: C₂₆H₃₂N₂O₄S
• 分子量: 468.617
• InChiKey: HJPYGLSWGZSYIF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  33
• 可旋转键数：
  11
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  120
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-[1-Benzyl-3-(carbamoyl-hydroxy-methyl)-2-ethyl-1H-indol-5-ylsulfanyl]-propionic acid tert-butyl ester 在 三乙基硅烷 、 三氟乙酸 作用下， 反应 2.0h， 以84%的产率得到3-(1-Benzyl-3-carbamoylmethyl-2-ethyl-1H-indol-5-ylsulfanyl)-propionic 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：

  2-ethyl-5-methoxy-1-(phenylmethyl)-1H-indole 在 sodium hydroxide 、 sodium tetrahydroborate 、 迭氮酸 、 三溴化硼 、 sodium hydride 、 potassium carbonate 、 二甲基亚砜 作用下， 以 二苯醚 、 乙醇 、 二氯甲烷 、 丁酮 为溶剂， 反应 79.0h， 生成 3-[1-Benzyl-3-(carbamoyl-hydroxy-methyl)-2-ethyl-1H-indol-5-ylsulfanyl]-propionic acid tert-butyl 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