methyl 4-(3,4-dihydro-1H-pyrido[4,3-b]indol-2(5H)-yl)butanoate | 1354547-69-5

• 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: methyl 4-(3,4-dihydro-1H-pyrido[4,3-b]indol-2(5H)-yl)butanoate
• CAS: 1354547-69-5
• 化学式: C₁₆H₂₀N₂O₂
• 分子量: 272.347
• InChiKey: KSBMDSLKJIGHGN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.48
• 重原子数：
  20.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  45.33
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  methyl 4-(3,4-dihydro-1H-pyrido[4,3-b]indol-2(5H)-yl)butanoate 在 氨 作用下， 以 甲醇 、 水 为溶剂， 反应 14.0h， 以54%的产率得到4-(3,4-dihydro-1H-pyrido[4,3-b]indol-2(5H)-yl)butanamide
  参考文献：
  名称：

  Second-Generation Histone Deacetylase 6 Inhibitors Enhance the Immunosuppressive Effects of Foxp3+ T-Regulatory Cells

  摘要：

  Second-generation Tubastatin A analogues were synthesized and evaluated for their ability to inhibit selectively histone deacetylase 6 (HDAC6). Substitutions to the carboline cap group were well-tolerated with substitution at the 2-position of both beta- and gamma-carbolines being optimal for HDAC6 activity and selectivity. Some compounds in this series were determined to have subnanomolar activity at HDAC6 with more than 7000 fold selectivity for HDAC6 versus HDAC1. Selected compounds were then evaluated for their ability to augment the immunosuppressive effect of Foxp3+ regulatory T cells. All compounds tested were found to enhance the ability of regulatory T cells to inhibit the mitotic division of effector T cells both in vitro and in vivo, suggesting that further investigation into the use of these compounds for the treatment of autoimmune disorders is warranted.

  DOI：

  10.1021/jm200773h
• 作为产物：
  描述：

  2-苄基-2,3,4,5-四氢-1H-吡啶并[4,3-b]吲哚 在 palladium 10% on activated carbon 、 氢气 、 三乙胺 作用下， 以 乙醇 、 水 、 乙腈 为溶剂， 20.0~70.0 ℃ 、101.33 kPa 条件下， 反应 26.0h， 生成 methyl 4-(3,4-dihydro-1H-pyrido[4,3-b]indol-2(5H)-yl)butanoate
  参考文献：
  名称：

  Second-Generation Histone Deacetylase 6 Inhibitors Enhance the Immunosuppressive Effects of Foxp3+ T-Regulatory Cells

  摘要：

  Second-generation Tubastatin A analogues were synthesized and evaluated for their ability to inhibit selectively histone deacetylase 6 (HDAC6). Substitutions to the carboline cap group were well-tolerated with substitution at the 2-position of both beta- and gamma-carbolines being optimal for HDAC6 activity and selectivity. Some compounds in this series were determined to have subnanomolar activity at HDAC6 with more than 7000 fold selectivity for HDAC6 versus HDAC1. Selected compounds were then evaluated for their ability to augment the immunosuppressive effect of Foxp3+ regulatory T cells. All compounds tested were found to enhance the ability of regulatory T cells to inhibit the mitotic division of effector T cells both in vitro and in vivo, suggesting that further investigation into the use of these compounds for the treatment of autoimmune disorders is warranted.

  DOI：

  10.1021/jm200773h