3-((benzyloxy)methyl)-1-oxo-N-(thiazol-2-yl)-1,2,3,4-tetrahydropyrazino[1,2-a]indole-7-carboxamide | 1025012-40-1

• 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-((benzyloxy)methyl)-1-oxo-N-(thiazol-2-yl)-1,2,3,4-tetrahydropyrazino[1,2-a]indole-7-carboxamide
• CAS: 1025012-40-1
• 化学式: C₂₃H₂₀N₄O₃S
• 分子量: 432.503
• InChiKey: MDFHZNLHCWLALE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.68
• 重原子数：
  31.0
• 可旋转键数：
  6.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  85.25
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  3-((benzyloxy)methyl)-1-oxo-N-(thiazol-2-yl)-1,2,3,4-tetrahydropyrazino[1,2-a]indole-7-carboxamide 、 溶剂黄146 在 氢溴酸 作用下， 反应 1.5h， 生成
  参考文献：
  名称：

  Synthesis and SAR studies of indole-based MK2 inhibitors

  摘要：

  Chemistry has been developed to specifically functionalize two structurally similar classes of indole-based MK2 inhibitors at positions prompted by a combination of X-ray crystallographic and computer assisted drug design. A gain in molecular potency was obtained by introducing aminomethyl groups to the lactam rings of 6-arylcarbamoyl-tetrahydro-beta-carbolinone and 6-arylcarbamoyl-dihydropyrazino[1,2-a] indolone MK2 inhibitors. In addition, improvements in molecular potency were achieved by expansion of the lactam from a 6- to 7-membered ring leading to 7-arylcarbamoyl-tetrahydro-[1,4] diazepino[1,2-a]indolones. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.01.119
• 作为产物：
  描述：

  2-氨基噻唑 、 3-((benzyloxy)methyl)-1-oxo-1,2,3,4-tetrahydropyrazino[1,2-a]indole-7-carboxylic acid 在 4-二甲氨基吡啶 1-羟基苯并三唑 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 、 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 14.0h， 以94%的产率得到3-((benzyloxy)methyl)-1-oxo-N-(thiazol-2-yl)-1,2,3,4-tetrahydropyrazino[1,2-a]indole-7-carboxamide
  参考文献：
  名称：

  Synthesis and SAR studies of indole-based MK2 inhibitors

  摘要：

  Chemistry has been developed to specifically functionalize two structurally similar classes of indole-based MK2 inhibitors at positions prompted by a combination of X-ray crystallographic and computer assisted drug design. A gain in molecular potency was obtained by introducing aminomethyl groups to the lactam rings of 6-arylcarbamoyl-tetrahydro-beta-carbolinone and 6-arylcarbamoyl-dihydropyrazino[1,2-a] indolone MK2 inhibitors. In addition, improvements in molecular potency were achieved by expansion of the lactam from a 6- to 7-membered ring leading to 7-arylcarbamoyl-tetrahydro-[1,4] diazepino[1,2-a]indolones. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.01.119