ethyl (2S,3aS,7aS)-N-tert-butoxycarbonyl-octahydro-1H-indole-2-carboxylate | 851702-75-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: ethyl (2S,3aS,7aS)-N-tert-butoxycarbonyl-octahydro-1H-indole-2-carboxylate
• 英文别名: 1-O-tert-butyl 2-O-ethyl (2S,3aS,7aS)-2,3,3a,4,5,6,7,7a-octahydroindole-1,2-dicarboxylate
• CAS: 851702-75-5
• 化学式: C₁₆H₂₇NO₄
• 分子量: 297.395
• InChiKey: QAGKBXQSXWOCSN-AVGNSLFASA-N

物化性质

• 沸点：
  373.2±25.0 °C(Predicted)
• 密度：
  1.089±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  55.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl (2S,3aS,7aS)-N-tert-butoxycarbonyl-octahydro-1H-indole-2-carboxylate 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 生成 ethyl (2α, 3aβ, 7aβ)-octahydro-1H-indole-2-carboxylate
  参考文献：
  名称：

  ( R )-3-Amino-1-((3a S ,7a S )-octahydro-1 H -indol-1-yl)-4-(2,4,5-trifluorophenyl)butan-1-one derivatives as potent inhibitors of dipeptidyl peptidase-4: Design, synthesis, biological evaluation, and molecular modeling

  摘要：

  A series of (R)-3-amino-1-((3aS,7aS)-octahydro-1H-indol-1-yl)-4-(2,4,5-trifluorophenyl)butan-1-one derivatives was designed, synthesized, and evaluated as novel inhibitors of dipeptidyl peptidase-4 (DPP-4) for the treatment of type 2 diabetes. Most of the synthesized compounds demonstrated good inhibition activities against DPP-4. Among these, compounds 3e, 4c, 4l, and 4n exhibited prominent inhibition activities against DPP-4, with IC(50)s of 0.07, 0.07, 0.14, and 0.17 mu M, respectively. The possible binding modes of compounds 3e and 4n with dipeptidyl peptidase-4 were also explored by molecular docking simulation. These potent DPP-4 inhibitors were optimized for the absorption, distribution, metabolism, and excretion (ADME) properties, and compound 4n displayed an attractive pharmacokinetic profile (F = 96.3%, t(1/2) = 10.5 h). (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2014.09.051
• 作为产物：
  描述：

  (2S,3aS,7aS)-八氢吲哚-2-羧酸 在 4-二甲氨基吡啶 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 生成 ethyl (2S,3aS,7aS)-N-tert-butoxycarbonyl-octahydro-1H-indole-2-carboxylate
  参考文献：
  名称：

  ( R )-3-Amino-1-((3a S ,7a S )-octahydro-1 H -indol-1-yl)-4-(2,4,5-trifluorophenyl)butan-1-one derivatives as potent inhibitors of dipeptidyl peptidase-4: Design, synthesis, biological evaluation, and molecular modeling

  摘要：

  A series of (R)-3-amino-1-((3aS,7aS)-octahydro-1H-indol-1-yl)-4-(2,4,5-trifluorophenyl)butan-1-one derivatives was designed, synthesized, and evaluated as novel inhibitors of dipeptidyl peptidase-4 (DPP-4) for the treatment of type 2 diabetes. Most of the synthesized compounds demonstrated good inhibition activities against DPP-4. Among these, compounds 3e, 4c, 4l, and 4n exhibited prominent inhibition activities against DPP-4, with IC(50)s of 0.07, 0.07, 0.14, and 0.17 mu M, respectively. The possible binding modes of compounds 3e and 4n with dipeptidyl peptidase-4 were also explored by molecular docking simulation. These potent DPP-4 inhibitors were optimized for the absorption, distribution, metabolism, and excretion (ADME) properties, and compound 4n displayed an attractive pharmacokinetic profile (F = 96.3%, t(1/2) = 10.5 h). (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2014.09.051

文献信息

• Synthesis of New Perhydroindole Derivatives and Their Evaluation in Ruthenium-Catalyzed Hydrogen Transfer Reduction
  作者：Benoît Liégault、Xiaoping Tang、Christian Bruneau、Jean-Luc Renaud

  DOI：10.1002/ejoc.200700476

  日期：2008.2

  New perhydroindole derivatives were synthesized with good yields and evaluated as chiral ligands in the RuII-catalyzed hydride transfer reduction of acetophenone. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)

  以良好的收率合成了新的全氢吲哚衍生物，并在 RuII 催化的苯乙酮氢化物转移还原中作为手性配体进行了评估。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)