(7R,9S)-7,9-diethyl-3-(2-phenylethyl)-1-phenyl-1,3,8-triaza-spiro[4.5]decane-2,4-dione | 1008746-95-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: (7R,9S)-7,9-diethyl-3-(2-phenylethyl)-1-phenyl-1,3,8-triaza-spiro[4.5]decane-2,4-dione
• 英文别名: (7S,9R)-7,9-diethyl-1-phenyl-3-(2-phenylethyl)-1,3,8-triazaspiro[4.5]decane-2,4-dione
• CAS: 1008746-95-9
• 化学式: C₂₅H₃₁N₃O₂
• 分子量: 405.54
• InChiKey: QXIBZXMYFNEWGV-KEVCNVLYSA-N

物化性质

• 熔点：
  146-147 °C
• 沸点：
  542.2±60.0 °C(predicted)
• 密度：
  1.19±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  30
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  52.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  、 乙基溴苯 在 potassium carbonate 作用下， 以 乙腈 为溶剂， 反应 16.0h， 以62%的产率得到(7R,9S)-7,9-diethyl-3-(2-phenylethyl)-1-phenyl-1,3,8-triaza-spiro[4.5]decane-2,4-dione
  参考文献：
  名称：

  In Search of Novel Agents for Therapy of Tropical Diseases and Human Immunodeficiency Virus

  摘要：

  Malaria, sleeping sickness, Chagas' disease, Aleppo boil, and AIDS are among the tropical diseases causing millions of infections and cases of deaths per year because only inefficient chemotherapy is available. Since the targeting of the enzymes of the polyamine pathway may provide novel therapy options, we aimed to inhibit the deoxyhypusine hydroxylase, which is an important step in the biosynthesis of the eukaryotic initiation factor 5A. In order to identify new lead compounds, piperidines were produced and biologically evaluated. The 3,5-diethyl piperidone-3,5-dicarboxylates 11 and 13 substituted with 4-nitrophenyl rings in the 2 and 6 positions were found to be active against Trypanosoma brucei brucei and Plasmodium falciparum combined with low cytotoxicity against macrophages. The corresponding monocarboxylates are only highly active against the T. brucei brucei. The piperidine oximether 53 demonstrated the highest plasmodicidal activity. Moreover, compounds 11 and 53 were also able to inhibit replication of HIV-1.

  DOI：

  10.1021/jm070763y

文献信息

• In Search of Novel Agents for Therapy of Tropical Diseases and Human Immunodeficiency Virus
  作者：Tim Goebel、Daniela Ulmer、Holger Projahn、Jessica Kloeckner、Eberhard Heller、Melanie Glaser、Alicia Ponte-Sucre、Sabine Specht、Salem Ramadan Sarite、Achim Hoerauf、Annette Kaiser、Ilona Hauber、Joachim Hauber、Ulrike Holzgrabe

  DOI：10.1021/jm070763y

  日期：2008.1.1

  Malaria, sleeping sickness, Chagas' disease, Aleppo boil, and AIDS are among the tropical diseases causing millions of infections and cases of deaths per year because only inefficient chemotherapy is available. Since the targeting of the enzymes of the polyamine pathway may provide novel therapy options, we aimed to inhibit the deoxyhypusine hydroxylase, which is an important step in the biosynthesis of the eukaryotic initiation factor 5A. In order to identify new lead compounds, piperidines were produced and biologically evaluated. The 3,5-diethyl piperidone-3,5-dicarboxylates 11 and 13 substituted with 4-nitrophenyl rings in the 2 and 6 positions were found to be active against Trypanosoma brucei brucei and Plasmodium falciparum combined with low cytotoxicity against macrophages. The corresponding monocarboxylates are only highly active against the T. brucei brucei. The piperidine oximether 53 demonstrated the highest plasmodicidal activity. Moreover, compounds 11 and 53 were also able to inhibit replication of HIV-1.