(2S),(4S)-3-(2-azido-3-ethyl-1-oxopentyl)-4-(phenylmethyl)-2-oxazolidinone | 544437-61-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (2S),(4S)-3-(2-azido-3-ethyl-1-oxopentyl)-4-(phenylmethyl)-2-oxazolidinone
• 英文别名: (4S)-3-[(2S)-2-azido-3-ethylpentanoyl]-4-benzyl-1,3-oxazolidin-2-one
• CAS: 544437-61-8
• 化学式: C₁₇H₂₂N₄O₃
• 分子量: 330.387
• InChiKey: HTUPSTADXKQNQA-GJZGRUSLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  61
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2S),(4S)-3-(2-azido-3-ethyl-1-oxopentyl)-4-(phenylmethyl)-2-oxazolidinone 在 lithium hydroxide monohydrate 作用下， 以 四氢呋喃 、 水 为溶剂， 以77%的产率得到2(S)-azido-3-ethylpentanoic acid
  参考文献：
  名称：

  Discovery of Begacestat, a Notch-1-Sparing γ-Secretase Inhibitor for the Treatment of Alzheimer’s Disease

  摘要：

  SAR on HTS hits I and 2 led to the potent, Notch-l-sparing GSI 9, which lowered brain A beta in Tg2576 mice at 100 mg/kg po. Converting the metabolically labile methyl groups in 9 to trifluoromethyl groups afforded the more stable analogue 10, which had improved in vivo potency. Further side chain modification afforded the potent Notch-1-sparing GSI begacestat (5). which was selected for development for the treatment of Alzheimer's disease.

  DOI：

  10.1021/jm801252w
• 作为产物：
  描述：

  (S)-4-benzyl-3-(3-ethylpentanoyl)oxazolidin-2-one 在 双(三甲基硅烷基)氨基钾 、 2,4,6-三异丙基苯磺酰叠氮化物 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 3.88h， 以56%的产率得到(2S),(4S)-3-(2-azido-3-ethyl-1-oxopentyl)-4-(phenylmethyl)-2-oxazolidinone
  参考文献：
  名称：

  Discovery of Begacestat, a Notch-1-Sparing γ-Secretase Inhibitor for the Treatment of Alzheimer’s Disease

  摘要：

  SAR on HTS hits I and 2 led to the potent, Notch-l-sparing GSI 9, which lowered brain A beta in Tg2576 mice at 100 mg/kg po. Converting the metabolically labile methyl groups in 9 to trifluoromethyl groups afforded the more stable analogue 10, which had improved in vivo potency. Further side chain modification afforded the potent Notch-1-sparing GSI begacestat (5). which was selected for development for the treatment of Alzheimer's disease.

  DOI：

  10.1021/jm801252w