[3-[(2R)-2-[[(2R)-2-hydroxy-2-(3-hydroxyphenyl)ethyl]-[(2-methylpropan-2-yl)oxycarbonyl]amino]propyl]-1H-indol-7-yl] methanesulfonate | 884331-11-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: [3-[(2R)-2-[[(2R)-2-hydroxy-2-(3-hydroxyphenyl)ethyl]-[(2-methylpropan-2-yl)oxycarbonyl]amino]propyl]-1H-indol-7-yl] methanesulfonate
• CAS: 884331-11-7
• 化学式: C₂₅H₃₂N₂O₇S
• 分子量: 504.604
• InChiKey: PPMRYAWVGHOWJA-IERDGZPVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  35
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  138
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  [3-[(2R)-2-[[(2R)-2-hydroxy-2-(3-hydroxyphenyl)ethyl]-[(2-methylpropan-2-yl)oxycarbonyl]amino]propyl]-1H-indol-7-yl] methanesulfonate 在 盐酸 、 三乙胺 作用下， 以 二氯甲烷 、 乙酸乙酯 为溶剂， 生成 [3-[(1R)-1-hydroxy-2-[[(2R)-1-(7-methylsulfonyloxy-1H-indol-3-yl)propan-2-yl]amino]ethyl]phenyl] benzenesulfonate
  参考文献：
  名称：

  Tryptamine-based human β3-adrenergic receptor agonists. Part 3: Improved oral bioavailability via modification of the sulfonamide moiety

  摘要：

  The continued SAR investigation of tryptamine-based human beta(3)-adrenergic receptor (AR) agonists is reported. Prior efforts resulted in the identification of 2 as a potent beta(3)-AR agonist. Further modification of the left side arylsulfonamide portion in 2 provided compounds with good cell permeability, which have potent agonistic activity for beta(3)-AR. Cinnamylamine analog 16i exhibited an excellent agonistic profile in vitro and good oral bioavailability in rats. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.12.033
• 作为产物：
  描述：

  (R)-1-(3-(benzyloxy)phenyl)-2-bromoethan-1-ol 在 palladium dihydroxide 咪唑 、 盐酸 、 氢气 、 N,N-二异丙基乙胺 、 potassium iodide 作用下， 以 乙醇 、 氯仿 、 乙酸乙酯 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 生成 [3-[(2R)-2-[[(2R)-2-hydroxy-2-(3-hydroxyphenyl)ethyl]-[(2-methylpropan-2-yl)oxycarbonyl]amino]propyl]-1H-indol-7-yl] methanesulfonate
  参考文献：
  名称：

  Tryptamine-based human β3-adrenergic receptor agonists. Part 3: Improved oral bioavailability via modification of the sulfonamide moiety

  摘要：

  The continued SAR investigation of tryptamine-based human beta(3)-adrenergic receptor (AR) agonists is reported. Prior efforts resulted in the identification of 2 as a potent beta(3)-AR agonist. Further modification of the left side arylsulfonamide portion in 2 provided compounds with good cell permeability, which have potent agonistic activity for beta(3)-AR. Cinnamylamine analog 16i exhibited an excellent agonistic profile in vitro and good oral bioavailability in rats. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.12.033