dimethyl (2R,6S)-4,4-dihydroxy-2,6-dimethyl-piperidinium-3,5-dicarboxylate hydrobromide | 1309479-07-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: dimethyl (2R,6S)-4,4-dihydroxy-2,6-dimethyl-piperidinium-3,5-dicarboxylate hydrobromide
• 英文别名: dimethyl (2R,6S)-4,4-dihydroxy-2,6-dimethylpiperidine-3,5-dicarboxylate;hydrobromide
• CAS: 1309479-07-9
• 化学式: BrH*C₁₁H₁₉NO₆
• 分子量: 342.187
• InChiKey: CURUDKSSDNSWNR-RHSYLKOPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.8
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  105
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  dimethyl (2R,6S)-4,4-dihydroxy-2,6-dimethyl-piperidinium-3,5-dicarboxylate hydrobromide 在 盐酸 作用下， 以95%的产率得到(2R,6S)-2,6-dimethyl-4-oxopiperidinium chloride
  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
• 作为产物：
  描述：

  聚合甲醛 、 1,3-丙酮二羧酸二甲酯 在 溴化铵 作用下， 以62%的产率得到dimethyl (2R,6S)-4,4-dihydroxy-2,6-dimethyl-piperidinium-3,5-dicarboxylate hydrobromide
  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