2-amino-N-[(2S)-3-(1H-indol-3-yl)-1-oxo-1-[(3S)-2-oxospiro[1H-indole-3,4'-azepane]-1'-yl]propan-2-yl]-2-methylpropanamide;2,2,2-trifluoroacetic acid | 1450600-62-0

• 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: 2-amino-N-[(2S)-3-(1H-indol-3-yl)-1-oxo-1-[(3S)-2-oxospiro[1H-indole-3,4'-azepane]-1'-yl]propan-2-yl]-2-methylpropanamide;2,2,2-trifluoroacetic acid
• CAS: 1450600-62-0
• 化学式: C₂HF₃O₂*C₂₈H₃₃N₅O₃
• 分子量: 601.626
• InChiKey: LHEBIGNQQFBTOS-DVASCVOVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.47
• 重原子数：
  43
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  158
• 氢给体数：
  5
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  2-amino-N-[(2S)-3-(1H-indol-3-yl)-1-oxo-1-[(3S)-2-oxospiro[1H-indole-3,4'-azepane]-1'-yl]propan-2-yl]-2-methylpropanamide;2,2,2-trifluoroacetic acid 、 乙酸酐 在 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 以75%的产率得到2-acetamido-N-[(2S)-3-(1H-indol-3-yl)-1-oxo-1-[(3S)-2-oxospiro[1H-indole-3,4'-azepane]-1'-yl]propan-2-yl]-2-methylpropanamide
  参考文献：
  名称：

  Antiproliferative activity on human prostate carcinoma cell lines of new peptidomimetics containing the spiroazepinoindolinone scaffold

  摘要：

  Peptidomimetics containing the spiroazepinoindolinone scaffold were designed and synthesized in order to ascertain their antiproliferative activity on the DU-145 human prostatic carcinoma cell line. Ethyl 2'-oxa-1,2,3,5,6,7-hexahydrospiro[4H-azepine-4,3'-3H-indole]-1'-carboxylate scaffold was functionalized at nitrogen azepino ring with Aib-(L/D)Trp-OH dipeptides. Combining the different stereochemistries of the scaffold and the tryptophan, diastereoisomeric peptidomimetics were prepared and tested. Their biological activity was evaluated by proliferation studies proving that the isomer containing S spiroazepino-indolinone scaffold and L tryptophan is the most active compound. Docking studies confirmed that the active peptidomimetic could bind the GHSR-la receptor with docking scores comparable with those of well-known agonists even though with a somewhat different binding mode. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.06.006
• 作为产物：
  描述：

  tert-butyl ((S)-3-(1H-indol-3-yl)-1-oxo-1-((S)-2'-oxospiro[azepane-4,3'-indolin]-1-yl)propan-2-yl)carbamate 在 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 21.5h， 生成 2-amino-N-[(2S)-3-(1H-indol-3-yl)-1-oxo-1-[(3S)-2-oxospiro[1H-indole-3,4'-azepane]-1'-yl]propan-2-yl]-2-methylpropanamide;2,2,2-trifluoroacetic acid
  参考文献：
  名称：

  Antiproliferative activity on human prostate carcinoma cell lines of new peptidomimetics containing the spiroazepinoindolinone scaffold

  摘要：

  Peptidomimetics containing the spiroazepinoindolinone scaffold were designed and synthesized in order to ascertain their antiproliferative activity on the DU-145 human prostatic carcinoma cell line. Ethyl 2'-oxa-1,2,3,5,6,7-hexahydrospiro[4H-azepine-4,3'-3H-indole]-1'-carboxylate scaffold was functionalized at nitrogen azepino ring with Aib-(L/D)Trp-OH dipeptides. Combining the different stereochemistries of the scaffold and the tryptophan, diastereoisomeric peptidomimetics were prepared and tested. Their biological activity was evaluated by proliferation studies proving that the isomer containing S spiroazepino-indolinone scaffold and L tryptophan is the most active compound. Docking studies confirmed that the active peptidomimetic could bind the GHSR-la receptor with docking scores comparable with those of well-known agonists even though with a somewhat different binding mode. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.06.006

文献信息

• Antiproliferative activity on human prostate carcinoma cell lines of new peptidomimetics containing the spiroazepinoindolinone scaffold
  作者：Sara Pellegrino、Massimiliano Ruscica、Paolo Magni、Giulio Vistoli、Maria Luisa Gelmi

  DOI：10.1016/j.bmc.2013.06.006

  日期：2013.9

  Peptidomimetics containing the spiroazepinoindolinone scaffold were designed and synthesized in order to ascertain their antiproliferative activity on the DU-145 human prostatic carcinoma cell line. Ethyl 2'-oxa-1,2,3,5,6,7-hexahydrospiro[4H-azepine-4,3'-3H-indole]-1'-carboxylate scaffold was functionalized at nitrogen azepino ring with Aib-(L/D)Trp-OH dipeptides. Combining the different stereochemistries of the scaffold and the tryptophan, diastereoisomeric peptidomimetics were prepared and tested. Their biological activity was evaluated by proliferation studies proving that the isomer containing S spiroazepino-indolinone scaffold and L tryptophan is the most active compound. Docking studies confirmed that the active peptidomimetic could bind the GHSR-la receptor with docking scores comparable with those of well-known agonists even though with a somewhat different binding mode. (C) 2013 Elsevier Ltd. All rights reserved.