Methanesulfonic acid 3-((R)-2-{tert-butoxycarbonyl-[(R)-2-hydroxy-2-(3-nitro-phenyl)-ethyl]-amino}-propyl)-1H-indol-7-yl ester | 776302-72-8

• 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-{tert-butoxycarbonyl-[(R)-2-hydroxy-2-(3-nitro-phenyl)-ethyl]-amino}-propyl)-1H-indol-7-yl ester
• 英文别名: [3-[(2R)-2-[[(2R)-2-hydroxy-2-(3-nitrophenyl)ethyl]-[(2-methylpropan-2-yl)oxycarbonyl]amino]propyl]-1H-indol-7-yl] methanesulfonate
• CAS: 776302-72-8
• 化学式: C₂₅H₃₁N₃O₈S
• 分子量: 533.602
• InChiKey: MQLUPUVSXICYLD-IERDGZPVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  37
• 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：
  163
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  Methanesulfonic acid 3-((R)-2-{tert-butoxycarbonyl-[(R)-2-hydroxy-2-(3-nitro-phenyl)-ethyl]-amino}-propyl)-1H-indol-7-yl ester 在 铁粉 、 氯化铵 作用下， 以 乙醇 为溶剂， 生成 Methanesulfonic acid 3-((R)-2-{[(R)-2-(3-amino-phenyl)-2-hydroxy-ethyl]-tert-butoxycarbonyl-amino}-propyl)-1H-indol-7-yl ester
  参考文献：
  名称：

  Tryptamine-based human β3-adrenergic receptor agonists. Part 2: SAR of the methylene derivatives

  摘要：

  A series of tryptamine derivatives with modified sulfonamide were designed, synthesized, and evaluated for their ability to stimulate CAMP accumulation in CHO cells expressing the cloned human beta(3)-adrenergic receptor (AR). For this series of compounds, our objective was to symmetrize the a-position of the tryptamine moiety maintaining its activity and reducing the cost of production. Compound 11h, having m-aminobenzene, exhibited excellent agonistic activity for beta(3)-AR with excellent subtype selectivity. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.09.054
• 作为产物：
  描述：

  (R)-(-)-(3-硝基苯基)环氧乙烷 以 氯仿 、 N,N-二甲基甲酰胺 为溶剂， 生成 Methanesulfonic acid 3-((R)-2-{tert-butoxycarbonyl-[(R)-2-hydroxy-2-(3-nitro-phenyl)-ethyl]-amino}-propyl)-1H-indol-7-yl ester
  参考文献：
  名称：

  Tryptamine-based human β3-adrenergic receptor agonists. Part 2: SAR of the methylene derivatives

  摘要：

  A series of tryptamine derivatives with modified sulfonamide were designed, synthesized, and evaluated for their ability to stimulate CAMP accumulation in CHO cells expressing the cloned human beta(3)-adrenergic receptor (AR). For this series of compounds, our objective was to symmetrize the a-position of the tryptamine moiety maintaining its activity and reducing the cost of production. Compound 11h, having m-aminobenzene, exhibited excellent agonistic activity for beta(3)-AR with excellent subtype selectivity. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.09.054

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.