8-(tert-butoxyformamido)-7,8,9,10-tetrahydro-6H-azepino<1,2-a>indole | 135440-79-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - Pyrroloazepines
• 英文名称: 8-(tert-butoxyformamido)-7,8,9,10-tetrahydro-6H-azepino<1,2-a>indole
• 英文别名: Tuemcelcqlgjow-uhfffaoysa-；tert-butyl N-(7,8,9,10-tetrahydro-6H-azepino[1,2-a]indol-8-yl)carbamate
• CAS: 135440-79-8
• 化学式: C₁₈H₂₄N₂O₂
• 分子量: 300.401
• InChiKey: TUEMCELCQLGJOW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  43.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  8-(tert-butoxyformamido)-7,8,9,10-tetrahydro-6H-azepino<1,2-a>indole 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 70.08h， 生成 3-<8-(tert-butoxyformamido)-7,8,9,10-tetrahydro-6H-azepino<1,2-a>indol-11-yl>-4-(1-methyl-3-indolyl)furan-2,5-dione
  参考文献：
  名称：

  Inhibitors of protein kinase C. 3. Potent and highly selective bisindolylmaleimides by conformational restriction

  摘要：

  The protein kinase inhibitor staurosporine has been used to design a series of selective bisindolylmaleimide inhibitors of protein kinase C (PKC). Guided by molecular graphics, conformational restriction of the cationic side chain has led to ATP competitive inhibitors of improved potency and selectivity. Two compounds have been further evaluated and were shown to inhibit PKC of human origin and prevent T-cell activation in a human allogeneic mixed lymphocyte reaction. One of these compounds was orally absorbed in mice and antagonized a phorbol ester induced paw edema in a dose-dependent manner. This compound also selectively inhibited the secondary T-cell mediated response in a developing adjuvant arthritis model in rats and provides evidence for the potential use of PKC inhibitors as therapeutic immunomodulators.

  DOI：

  10.1021/jm00053a003
• 作为产物：
  描述：

  ethyl 1-(4-ethoxy-4-oxobutyl)-1H-indole-2-carboxylate 在 sodium hydroxide 、 W-2 Raney nickel 、 potassium tert-butylate 、 硼酸 、 sodium hydride 、 三乙胺 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 水 为溶剂， 反应 77.5h， 生成 8-(tert-butoxyformamido)-7,8,9,10-tetrahydro-6H-azepino<1,2-a>indole
  参考文献：
  名称：

  Dieckmann / ring扩容方法制备四氢吡啶并和四氢氮杂环庚烷-[1,2-a]吲哚

  摘要：

  据报道，一般的Dieckmann /环膨胀方法用于稠合的[1,2-a]吲哚体系。这种方法已允许合成制备一系列有效和选择性的蛋白激酶C抑制剂所需的多种取代系统。

  DOI：

  10.1016/s0040-4020(01)86471-1

文献信息

• A Dieckmann/ring expansion approach to tetrahydropyrido- and tetrahydroazepino-[1,2-a]indoles
  作者：Rino A. Bit、Peter D. Davis、Christopher H. Hill、Elizabeth Keech、David R. Vesey

  DOI：10.1016/s0040-4020(01)86471-1

  日期：1991.1

  A general Dieckmann/ring expansion approach to fused [1,2-a]indole systems is reported. This approach has allowed the synthesis of a large variety of substituted systems required for the preparation of a series of potent and selective inhibitors of Protein Kinase C.

  据报道，一般的Dieckmann /环膨胀方法用于稠合的[1,2-a]吲哚体系。这种方法已允许合成制备一系列有效和选择性的蛋白激酶C抑制剂所需的多种取代系统。
• Inhibitors of protein kinase C. 3. Potent and highly selective bisindolylmaleimides by conformational restriction
  作者：Rino A. Bit、Peter D. Davis、Lucy H. Elliott、William Harris、Christopher H. Hill、Elizabeth Keech、Hari Kumar、Geoffrey Lawton、Anna Maw、John S. Nixon、David R. Vesey、Julie Wadsworth、Sandra E. Wilkinson

  DOI：10.1021/jm00053a003

  日期：1993.1

  The protein kinase inhibitor staurosporine has been used to design a series of selective bisindolylmaleimide inhibitors of protein kinase C (PKC). Guided by molecular graphics, conformational restriction of the cationic side chain has led to ATP competitive inhibitors of improved potency and selectivity. Two compounds have been further evaluated and were shown to inhibit PKC of human origin and prevent T-cell activation in a human allogeneic mixed lymphocyte reaction. One of these compounds was orally absorbed in mice and antagonized a phorbol ester induced paw edema in a dose-dependent manner. This compound also selectively inhibited the secondary T-cell mediated response in a developing adjuvant arthritis model in rats and provides evidence for the potential use of PKC inhibitors as therapeutic immunomodulators.