9,9a-dihydro-1H-imidazo[1,5-a]indole-1,3(2H)-dione | 769926-00-3

• 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: 9,9a-dihydro-1H-imidazo[1,5-a]indole-1,3(2H)-dione
• 英文别名: 3a,4-Dihydroimidazo[1,5-a]indole-1,3-dione
• CAS: 769926-00-3
• 化学式: C₁₀H₈N₂O₂
• 分子量: 188.186
• InChiKey: HCLVDXFSLLANBO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  49.4
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  9,9a-dihydro-1H-imidazo[1,5-a]indole-1,3(2H)-dione 在 N-溴代丁二酰亚胺(NBS) 、 偶氮二异丁腈 、 三乙胺 作用下， 以 四氢呋喃 、 四氯化碳 为溶剂， 反应 13.0h， 生成 Tetrahydroisoquinoline hydantoin derivative, 4a
  参考文献：
  名称：

  Design, synthesis and biological evaluation of new thalidomide analogues as TNF-α and IL-6 production inhibitors

  摘要：

  Several thalidomide analogues were synthesized and compared to thalidomide and its more active analogue, lenalidomide, for their ability to inhibit the production of the pro-inflammatory cytokine tumour necrosis factor (TNF)-alpha and interleukin (IL)-6 by LPS-activated peripheral blood mononuclear cells (PBMCs). Among these compounds, two analogues containing sulfonyl group displayed interesting downregulation of TNF-alpha and IL-6 production. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.12.031
• 作为产物：
  描述：

  potassium cyanate 、 吲哚啉-2-羧酸 在 盐酸 作用下， 以 水 为溶剂， 反应 3.0h， 以49%的产率得到9,9a-dihydro-1H-imidazo[1,5-a]indole-1,3(2H)-dione
  参考文献：
  名称：

  Design, synthesis and biological evaluation of new thalidomide analogues as TNF-α and IL-6 production inhibitors

  摘要：

  Several thalidomide analogues were synthesized and compared to thalidomide and its more active analogue, lenalidomide, for their ability to inhibit the production of the pro-inflammatory cytokine tumour necrosis factor (TNF)-alpha and interleukin (IL)-6 by LPS-activated peripheral blood mononuclear cells (PBMCs). Among these compounds, two analogues containing sulfonyl group displayed interesting downregulation of TNF-alpha and IL-6 production. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.12.031