3-(azidomethyl)-1-oxo-N-(thiazol-2-yl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-6-carboxamide | 1025012-22-9

• 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-(azidomethyl)-1-oxo-N-(thiazol-2-yl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-6-carboxamide
• CAS: 1025012-22-9
• 化学式: C₁₆H₁₃N₇O₂S
• 分子量: 367.391
• InChiKey: AVNHNNMSORNWFA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.84
• 重原子数：
  26.0
• 可旋转键数：
  4.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  135.64
• 氢给体数：
  3.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  3-(azidomethyl)-1-oxo-N-(thiazol-2-yl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-6-carboxamide 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 、 N,N-二甲基乙酰胺 为溶剂， 反应 2.0h， 以65%的产率得到3-aminomethyl-1-oxo-2,3,4,9-tetrahydro-1H-β-carboline-6-carboxylic acid thiazol-2-yl amide
  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-azidomethyl-1-oxo-2,3,4,9-tetrahydro-1H-βb-carboline-6-carboxylic acid 在 N-羟基-7-氮杂苯并三氮唑 、 N,N-二异丙基乙胺 、 N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 48.0h， 以85%的产率得到3-(azidomethyl)-1-oxo-N-(thiazol-2-yl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-6-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