(S)-4-benzyl-3-((S)-4-((1R,3R,5S)-3-(2-methyl-3H-imidazo[4,5-b]pyridin-3-yl)-8-azabicyclo[3.2.1]octan-8-yl)-2-phenylbutanoyl)oxazolidin-2-one | 1225034-58-1

• 分子结构分类: 有机化合物 - 生物碱及其衍生物
• 英文名称: (S)-4-benzyl-3-((S)-4-((1R,3R,5S)-3-(2-methyl-3H-imidazo[4,5-b]pyridin-3-yl)-8-azabicyclo[3.2.1]octan-8-yl)-2-phenylbutanoyl)oxazolidin-2-one
• CAS: 1225034-58-1
• 化学式: C₃₄H₃₇N₅O₃
• 分子量: 563.699
• InChiKey: TXQHATBHMPRSQO-RULDIGERSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.67
• 重原子数：
  42.0
• 可旋转键数：
  8.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  80.56
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  (S)-4-benzyl-3-((S)-4-((1R,3R,5S)-3-(2-methyl-3H-imidazo[4,5-b]pyridin-3-yl)-8-azabicyclo[3.2.1]octan-8-yl)-2-phenylbutanoyl)oxazolidin-2-one 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以98%的产率得到(S)-4-((1R,3R,5S)-3-(2-methyl-3H-imidazo[4,5-b]pyridin-3-yl)-8-azabicyclo[3.2.1]octan-8-yl)-2-phenylbutan-1-ol
  参考文献：
  名称：

  Discovery of novel (S)-α-phenyl-γ-amino butanamide containing CCR5 antagonists via functionality inversion approach

  摘要：

  By using functionality inversion approach, we identified a new scaffold containing (S)-alpha-phenyl-gamma-amino butanamide as CCR5 antagonists derived from the 1,3-propanediamine carboxamide pharmacophore protocol. The (2S)-2-phenyl-4-(8-aza-bicyclo[3.2.1]octan-8-yl)-butanamide derivatives display significantly high potency to antagonize CCR5 receptor with nanomolar IC50 values. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.02.023
• 作为产物：
  描述：

  3-((1R,3s,5S)-8-azabicyclo[3.2.1]octan-3-yl)-2-methyl-3H-imidazo[4,5-b]pyridine 、 (S)-4-((S)-4-benzyl-2-oxooxazolidin-3-yl)-4-oxo-3-phenylbutanal 在 三乙酰氧基硼氢化钠 、 溶剂黄146 作用下， 以 1,2-二氯乙烷 为溶剂， 生成 (S)-4-benzyl-3-((S)-4-((1R,3R,5S)-3-(2-methyl-3H-imidazo[4,5-b]pyridin-3-yl)-8-azabicyclo[3.2.1]octan-8-yl)-2-phenylbutanoyl)oxazolidin-2-one
  参考文献：
  名称：

  Discovery of novel (S)-α-phenyl-γ-amino butanamide containing CCR5 antagonists via functionality inversion approach

  摘要：

  By using functionality inversion approach, we identified a new scaffold containing (S)-alpha-phenyl-gamma-amino butanamide as CCR5 antagonists derived from the 1,3-propanediamine carboxamide pharmacophore protocol. The (2S)-2-phenyl-4-(8-aza-bicyclo[3.2.1]octan-8-yl)-butanamide derivatives display significantly high potency to antagonize CCR5 receptor with nanomolar IC50 values. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.02.023