(3S)-3-amino-1-methoxy-3,4-dihydroquinolin-2(1H)-one | 121989-61-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: (3S)-3-amino-1-methoxy-3,4-dihydroquinolin-2(1H)-one
• 英文别名: (3S)-3-amino-1-methoxy-3,4-dihydroquinolin-2-one
• CAS: 121989-61-5
• 化学式: C₁₀H₁₂N₂O₂
• 分子量: 192.217
• InChiKey: UYXSPCLQWKBUEW-QMMMGPOBSA-N

物化性质

• 沸点：
  303.3±52.0 °C(Predicted)
• 密度：
  1.27±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  55.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (3S)-3-amino-1-methoxy-3,4-dihydroquinolin-2(1H)-one 在 palladium on activated charcoal 盐酸 、 氢气 、 sodium hydride 、 三乙胺 作用下， 以 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 25.0 ℃ 、300.0 kPa 条件下， 反应 34.08h， 生成 [(S)-1-((R)-2,2-Dimethyl-[1,3]dioxolan-4-ylmethyl)-2-oxo-1,2,3,4-tetrahydro-quinolin-3-yl]-carbamic acid tert-butyl ester
  参考文献：
  名称：

  Development of potent, orally active 1-substituted-3,4-dihydro-2-quinolone glycogen phosphorylase inhibitors

  摘要：

  A series of substituted 3,4-dihydro-2-quinolone glycogen phosphorylase inhibitors, which have potential as antidiabetic agents, is described. Initial members of the series showed good enzyme inhibitory potency but poor physical properties. Optimisation of the 1-substituent led to 2,3-dihydroxypropyl compounds which showed good in vitro potency and improved physical properties, together with good DMPK profiles and acute in vivo efficacy in a rat model. X-ray crystallographic data are presented, showing an unexpected variety of binding orientations at the dimer interface site.

  DOI：

  10.1016/j.bmcl.2006.10.037
• 作为产物：
  描述：

  N-苄氧羰基-D-苯丙氨酸 在 palladium on activated charcoal 氢气 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 、 三氟乙酸 、 [双(三氟乙酰氧基)碘]苯 作用下， 以 二氯甲烷 、 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 20.0 ℃ 、100.0 kPa 条件下， 反应 12.0h， 生成 (3S)-3-amino-1-methoxy-3,4-dihydroquinolin-2(1H)-one
  参考文献：
  名称：

  Development of potent, orally active 1-substituted-3,4-dihydro-2-quinolone glycogen phosphorylase inhibitors

  摘要：

  A series of substituted 3,4-dihydro-2-quinolone glycogen phosphorylase inhibitors, which have potential as antidiabetic agents, is described. Initial members of the series showed good enzyme inhibitory potency but poor physical properties. Optimisation of the 1-substituent led to 2,3-dihydroxypropyl compounds which showed good in vitro potency and improved physical properties, together with good DMPK profiles and acute in vivo efficacy in a rat model. X-ray crystallographic data are presented, showing an unexpected variety of binding orientations at the dimer interface site.

  DOI：

  10.1016/j.bmcl.2006.10.037

文献信息

• Development of potent, orally active 1-substituted-3,4-dihydro-2-quinolone glycogen phosphorylase inhibitors
  作者：Alan M. Birch、Peter W. Kenny、Nikos G. Oikonomakos、Ludovic Otterbein、Paul Schofield、Paul R.O. Whittamore、Dave P. Whalley

  DOI：10.1016/j.bmcl.2006.10.037

  日期：2007.1

  A series of substituted 3,4-dihydro-2-quinolone glycogen phosphorylase inhibitors, which have potential as antidiabetic agents, is described. Initial members of the series showed good enzyme inhibitory potency but poor physical properties. Optimisation of the 1-substituent led to 2,3-dihydroxypropyl compounds which showed good in vitro potency and improved physical properties, together with good DMPK profiles and acute in vivo efficacy in a rat model. X-ray crystallographic data are presented, showing an unexpected variety of binding orientations at the dimer interface site.