ethyl 2-((1-(tert-butoxycarbonyl)piperidin-4-yl)methyl)-1-methyl-1H-benzo[d]imidazole-5-carboxylate | 1552311-91-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 英文名称: ethyl 2-((1-(tert-butoxycarbonyl)piperidin-4-yl)methyl)-1-methyl-1H-benzo[d]imidazole-5-carboxylate
• CAS: 1552311-91-7
• 化学式: C₂₂H₃₁N₃O₄
• 分子量: 401.506
• InChiKey: UHIIETAEBYOTHP-UHFFFAOYSA-N

物化性质

• 沸点：
  546.2±20.0 °C(predicted)
• 密度：
  1.19±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.94
• 重原子数：
  29.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  73.66
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  ethyl 2-((1-(tert-butoxycarbonyl)piperidin-4-yl)methyl)-1-methyl-1H-benzo[d]imidazole-5-carboxylate 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 18.0h， 以94%的产率得到2-((1-(tert-butoxycarbonyl)piperidin-4-yl)methyl)-1-methyl-1H-benzo[d]imidazole-5-carboxylic acid
  参考文献：
  名称：

  Fragment-based design of 3-aminopyridine-derived amides as potent inhibitors of human nicotinamide phosphoribosyltransferase (NAMPT)

  摘要：

  The fragment-based identification of two novel and potent biochemical inhibitors of the nicotinamide phosphoribosyltransferase (NAMPT) enzyme is described. These compounds (51 and 63) incorporate an amide moiety derived from 3-aminopyridine, and are thus structurally distinct from other known anti-NAMPT agents. Each exhibits potent inhibition of NAMPT biochemical activity (IC50=19 and 15 nM, respectively) as well as robust antiproliferative properties in A2780 cell culture experiments (IC50=121 and 99 nM, respectively). However, additional biological studies indicate that only inhibitor 51 exerts its A2780 cell culture effects via a NAMPT-mediated mechanism. The crystal structures of both 51 and 63 in complex with NAMPT are also independently described.

  DOI：

  10.1016/j.bmcl.2013.12.062
• 作为产物：
  描述：

  3-氨基-4-(甲胺基)苯甲酸乙酯 、 4-(2-氧代乙基)哌啶-1-羧酸叔丁酯 在 palladium 10% on activated carbon 、 氢气 作用下， 以 乙醇 为溶剂， 反应 48.0h， 以89%的产率得到ethyl 2-((1-(tert-butoxycarbonyl)piperidin-4-yl)methyl)-1-methyl-1H-benzo[d]imidazole-5-carboxylate
  参考文献：
  名称：

  Fragment-based design of 3-aminopyridine-derived amides as potent inhibitors of human nicotinamide phosphoribosyltransferase (NAMPT)

  摘要：

  The fragment-based identification of two novel and potent biochemical inhibitors of the nicotinamide phosphoribosyltransferase (NAMPT) enzyme is described. These compounds (51 and 63) incorporate an amide moiety derived from 3-aminopyridine, and are thus structurally distinct from other known anti-NAMPT agents. Each exhibits potent inhibition of NAMPT biochemical activity (IC50=19 and 15 nM, respectively) as well as robust antiproliferative properties in A2780 cell culture experiments (IC50=121 and 99 nM, respectively). However, additional biological studies indicate that only inhibitor 51 exerts its A2780 cell culture effects via a NAMPT-mediated mechanism. The crystal structures of both 51 and 63 in complex with NAMPT are also independently described.

  DOI：

  10.1016/j.bmcl.2013.12.062