tert-butyl [(1S)-1-({[5-(4-amino-8,9-dimethoxybenzo[c][2,7]naphthyridin-2-yl)pyridin-3-yl]oxy}methyl)propyl]carbamate | 1055963-94-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: tert-butyl [(1S)-1-({[5-(4-amino-8,9-dimethoxybenzo[c][2,7]naphthyridin-2-yl)pyridin-3-yl]oxy}methyl)propyl]carbamate
• 英文别名: tert-butyl N-[(2S)-1-[5-(4-amino-8,9-dimethoxybenzo[c][2,7]naphthyridin-2-yl)pyridin-3-yl]oxybutan-2-yl]carbamate
• CAS: 1055963-94-4
• 化学式: C₂₈H₃₃N₅O₅
• 分子量: 519.601
• InChiKey: HMRQSRGVKJPPDS-KRWDZBQOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  38
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  131
• 氢给体数：
  2
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  tert-butyl [(1S)-1-({[5-(4-amino-8,9-dimethoxybenzo[c][2,7]naphthyridin-2-yl)pyridin-3-yl]oxy}methyl)propyl]carbamate 在 盐酸 、 水 、 sodium hydroxide 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 6.0h， 生成 2-(5-([(2S)-2-aminobutyl]oxy)pyridin-3-yl)-8,9-dimethoxybenzo[c]-2,7-naphthyridin-4-amine
  参考文献：
  名称：

  The identification of 8,9-dimethoxy-5-(2-aminoalkoxy-pyridin-3-yl)-benzo[c][2,7]naphthyridin-4-ylamines as potent inhibitors of 3-phosphoinositide-dependent kinase-1 (PDK-1)

  摘要：

  A series of 8,9-dimethoxy-5-(2-aminoalkoxy-pyridin-3-yl)-benzo[c] [2,7]naphthyridin-4-ylamine-based inhibitors of 3-phosphoinositide-dependent kinase-1 (PDK-1) has been identified. Several examples appear to be potent and relatively selective inhibitors of PDK-1 over the related AGC kinases PKA, PKB/AKT, and p70S6K. The introduction of a stereochemical center beside the amino substituent on the aminoalkoxy-side chain had little effect upon the inhibitory activity against these enzymes, and X-ray crystallographic analyses of a representative pair of enantiomeric inhibitors bound to the active site of PDK-1 revealed comparable binding modes for each enantiomer. (C) 2009 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2009.12.036
• 作为产物：
  描述：

  tert-butyl N-[(2S)-1-[5-[2-(3-cyano-6,7-dimethoxyquinolin-4-yl)acetyl]pyridin-3-yl]oxybutan-2-yl]carbamate 在 ammonium acetate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成 tert-butyl [(1S)-1-({[5-(4-amino-8,9-dimethoxybenzo[c][2,7]naphthyridin-2-yl)pyridin-3-yl]oxy}methyl)propyl]carbamate
  参考文献：
  名称：

  The identification of 8,9-dimethoxy-5-(2-aminoalkoxy-pyridin-3-yl)-benzo[c][2,7]naphthyridin-4-ylamines as potent inhibitors of 3-phosphoinositide-dependent kinase-1 (PDK-1)

  摘要：

  A series of 8,9-dimethoxy-5-(2-aminoalkoxy-pyridin-3-yl)-benzo[c] [2,7]naphthyridin-4-ylamine-based inhibitors of 3-phosphoinositide-dependent kinase-1 (PDK-1) has been identified. Several examples appear to be potent and relatively selective inhibitors of PDK-1 over the related AGC kinases PKA, PKB/AKT, and p70S6K. The introduction of a stereochemical center beside the amino substituent on the aminoalkoxy-side chain had little effect upon the inhibitory activity against these enzymes, and X-ray crystallographic analyses of a representative pair of enantiomeric inhibitors bound to the active site of PDK-1 revealed comparable binding modes for each enantiomer. (C) 2009 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2009.12.036