Methanesulfonic acid 3-{(R)-2-[(R)-2-(3-benzyloxy-phenyl)-2-hydroxy-ethylamino]-propyl}-1H-indol-7-yl ester | 848072-87-7

• 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: Methanesulfonic acid 3-{(R)-2-[(R)-2-(3-benzyloxy-phenyl)-2-hydroxy-ethylamino]-propyl}-1H-indol-7-yl ester
• 英文别名: [3-[(2R)-2-[[(2R)-2-hydroxy-2-(3-phenylmethoxyphenyl)ethyl]amino]propyl]-1H-indol-7-yl] methanesulfonate
• CAS: 848072-87-7
• 化学式: C₂₇H₃₀N₂O₅S
• 分子量: 494.612
• InChiKey: NOUCOYNKCVTYDV-CLOONOSVSA-N

物化性质

• 沸点：
  729.4±60.0 °C(Predicted)
• 密度：
  1.294±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  35
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  109
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  Methanesulfonic acid 3-{(R)-2-[(R)-2-(3-benzyloxy-phenyl)-2-hydroxy-ethylamino]-propyl}-1H-indol-7-yl ester 在 palladium dihydroxide 氢气 作用下， 以 乙醇 、 氯仿 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
• 作为产物：
  描述：

  3-苄氧基苯乙酮 在 咪唑 、 盐酸 、 硼烷四氢呋喃络合物 、 phenyltrimethylammonium tribromide 、 N,N-二异丙基乙胺 、 potassium iodide 、 (R)-2-甲基-CBS-恶唑硼烷 作用下， 以 四氢呋喃 、 乙酸乙酯 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 生成 Methanesulfonic acid 3-{(R)-2-[(R)-2-(3-benzyloxy-phenyl)-2-hydroxy-ethylamino]-propyl}-1H-indol-7-yl ester
  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

文献信息

• Tryptamine-based human β3-adrenergic receptor agonists. Part 3: Improved oral bioavailability via modification of the sulfonamide moiety
  作者：Masaaki Sawa、Kazuhiro Mizuno、Hiroshi Harada、Hirotaka Tateishi、Yukiyo Arai、Shinya Suzuki、Mayumi Oue、Hiroshi Tsujiuchi、Yasuji Furutani、Shiro Kato

  DOI：10.1016/j.bmcl.2004.12.033

  日期：2005.2

  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.