Dimethyl-thiocarbamic acid O-(1-benzyl-2,7-dimethyl-1H-indol-5-yl) ester | 185501-64-8

• 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: Dimethyl-thiocarbamic acid O-(1-benzyl-2,7-dimethyl-1H-indol-5-yl) ester
• 英文别名: O-(1-benzyl-2,7-dimethylindol-5-yl) N,N-dimethylcarbamothioate
• CAS: 185501-64-8
• 化学式: C₂₀H₂₂N₂OS
• 分子量: 338.473
• InChiKey: BOQJOYHKJDPTKI-UHFFFAOYSA-N

物化性质

• 沸点：
  494.7±55.0 °C(Predicted)
• 密度：
  1.11±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  49.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  Dimethyl-thiocarbamic acid O-(1-benzyl-2,7-dimethyl-1H-indol-5-yl) ester 在 三乙基硅烷 、 sodium hydroxide 、 sodium tetrahydroborate 、 氨 、 sodium hydride 、 三氟乙酸 作用下， 以 二苯醚 、 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 58.75h， 生成 4-(1-Benzyl-3-carbamoylmethyl-2,7-dimethyl-1H-indol-5-ylsulfanyl)-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
• 作为产物：
  描述：

  5-甲氧基-2-甲基吲哚 在 sodium hydroxide 、 四甲基乙二胺 、 仲丁基锂 、 三溴化硼 、 sodium hydride 、 sodium cyanoborohydride 、 溶剂黄146 、 三氟乙酸 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 134.25h， 生成 Dimethyl-thiocarbamic acid O-(1-benzyl-2,7-dimethyl-1H-indol-5-yl) 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