methyl 5-({(2R)-2-[(tert-butoxycarbonyl)amino]-3-[3-(trifluoromethyl)phenyl]propyl}oxy)nicotinate | 1055969-12-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: methyl 5-({(2R)-2-[(tert-butoxycarbonyl)amino]-3-[3-(trifluoromethyl)phenyl]propyl}oxy)nicotinate
• 英文别名: methyl 5-[(2R)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-[3-(trifluoromethyl)phenyl]propoxy]pyridine-3-carboxylate
• CAS: 1055969-12-4
• 化学式: C₂₂H₂₅F₃N₂O₅
• 分子量: 454.446
• InChiKey: XKUOFISUKRVGIX-QGZVFWFLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  32
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  86.8
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  6,7-dimethoxy-4-methyl-3-cyanoquinoline 、 methyl 5-({(2R)-2-[(tert-butoxycarbonyl)amino]-3-[3-(trifluoromethyl)phenyl]propyl}oxy)nicotinate 在 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 为溶剂， 反应 3.5h， 生成 tert-butyl N-[(2R)-1-[5-[2-(3-cyano-6,7-dimethoxyquinolin-4-yl)acetyl]pyridin-3-yl]oxy-3-[3-(trifluoromethyl)phenyl]propan-2-yl]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
• 作为产物：
  描述：

  (2R)-tert-butyl {1-hydroxy-3-[3-(trifluoromethyl)phenyl]propan-2-yl}carbamate 、 5-羟基烟酸甲酯 在 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 为溶剂， 反应 3.17h， 生成 methyl 5-({(2R)-2-[(tert-butoxycarbonyl)amino]-3-[3-(trifluoromethyl)phenyl]propyl}oxy)nicotinate
  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