(5R)-(2-tert-butoxycarbonylamino-propoxy)-nicotinic acid methyl ester | 1055969-32-8

• 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: (5R)-(2-tert-butoxycarbonylamino-propoxy)-nicotinic acid methyl ester
• 英文别名: methyl 5-[(2R)-2-[(2-methylpropan-2-yl)oxycarbonylamino]propoxy]pyridine-3-carboxylate
• CAS: 1055969-32-8
• 化学式: C₁₅H₂₂N₂O₅
• 分子量: 310.35
• InChiKey: IWTULWIBNRCVJI-SNVBAGLBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  22
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  86.8
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  6,7-dimethoxy-4-methyl-3-cyanoquinoline 、 (5R)-(2-tert-butoxycarbonylamino-propoxy)-nicotinic acid methyl ester 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]oxypropan-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)-2-[(tert-butoxycarbonyl)amino]propyl methanesulfonate 、 5-羟基烟酸甲酯 在 caesium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 18.0h， 生成 (5R)-(2-tert-butoxycarbonylamino-propoxy)-nicotinic acid methyl ester
  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

文献信息

• 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)
  作者：Thomas Nittoli、Russell G. Dushin、Charles Ingalls、Katherine Cheung、M. Brawner Floyd、Heidi Fraser、Andrea Olland、Yongbo Hu、George Grosu、Xin Han

  DOI：10.1016/j.ejmech.2009.12.036

  日期：2010.4

  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.