[3-[(2R)-2-氨基丙基]-1H-吲哚-7-基]吡啶-3-磺酸酯 | 820216-43-1

• 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
• 中文名称: [3-[(2R)-2-氨基丙基]-1H-吲哚-7-基]吡啶-3-磺酸酯
• 英文名称: Pyridine-3-sulfonic acid 3-((R)-2-amino-propyl)-1H-indol-7-yl ester
• 英文别名: 3-[(2R)-2-Aminopropyl]-1H-indol-7-yl pyridine-3-sulfonate；[3-[(2R)-2-aminopropyl]-1H-indol-7-yl] pyridine-3-sulfonate
• CAS: 820216-43-1
• 化学式: C₁₆H₁₇N₃O₃S
• 分子量: 331.395
• InChiKey: BXDGYFABVYIVAD-LLVKDONJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  106
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  [3-[(2R)-2-氨基丙基]-1H-吲哚-7-基]吡啶-3-磺酸酯 在 盐酸 、 二乙基异丙基胺 、 potassium iodide 作用下， 以 乙醇 、 乙腈 为溶剂， 生成 Pyridine-3-sulfonic acid 3-(2-{(R)-(R)-2-hydroxy-2-[3-(thiophene-2-sulfonylamino)-phenyl]-ethylamino}-propyl)-1H-indol-7-yl ester
  参考文献：
  名称：

  Tryptamine-based human β3-adrenergic receptor agonists. Part 1: SAR studies of the 7-position of the indole ring

  摘要：

  A series of tryptamine-based 2-thiophenesulfonamide derivatives were prepared and their agonistic activity for the beta-adrenergic receptors (ARs) was evaluated. Compound 54, containing 7-methanesulfonyloxy tryptamine, was found to be a highly potent beta(3)-AR agonist (EC50 = 0.21 nM, IA = 97%) with excellent selectivity for the beta(3)-AR over the beta(1)- and beta(2)-ARs (210- and 86-fold, respectively). (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.10.035
• 作为产物：
  描述：

  (R)-3-(2-aminopropyl)-7-benzyloxyindole 在 palladium on activated charcoal 盐酸 、 TEA 、 甲酸铵 作用下， 以 甲醇 、 二氯甲烷 、 氯仿 、 乙酸乙酯 为溶剂， 生成 [3-[(2R)-2-氨基丙基]-1H-吲哚-7-基]吡啶-3-磺酸酯
  参考文献：
  名称：

  Tryptamine-based human β3-adrenergic receptor agonists. Part 1: SAR studies of the 7-position of the indole ring

  摘要：

  A series of tryptamine-based 2-thiophenesulfonamide derivatives were prepared and their agonistic activity for the beta-adrenergic receptors (ARs) was evaluated. Compound 54, containing 7-methanesulfonyloxy tryptamine, was found to be a highly potent beta(3)-AR agonist (EC50 = 0.21 nM, IA = 97%) with excellent selectivity for the beta(3)-AR over the beta(1)- and beta(2)-ARs (210- and 86-fold, respectively). (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.10.035

文献信息

• Tryptamine-based human β3-adrenergic receptor agonists. Part 1: SAR studies of the 7-position of the indole ring
  作者：Kazuhiro Mizuno、Masaaki Sawa、Hiroshi Harada、Hirotaka Tateishi、Mayumi Oue、Hiroshi Tsujiuchi、Yasuji Furutani、Shiro Kato

  DOI：10.1016/j.bmcl.2004.10.035

  日期：2004.12

  A series of tryptamine-based 2-thiophenesulfonamide derivatives were prepared and their agonistic activity for the beta-adrenergic receptors (ARs) was evaluated. Compound 54, containing 7-methanesulfonyloxy tryptamine, was found to be a highly potent beta(3)-AR agonist (EC50 = 0.21 nM, IA = 97%) with excellent selectivity for the beta(3)-AR over the beta(1)- and beta(2)-ARs (210- and 86-fold, respectively). (C) 2004 Elsevier Ltd. All rights reserved.