N-((1S,3R,5S)-3,5-Diamino-cyclohexyl)-propionamide | 479251-84-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: N-((1S,3R,5S)-3,5-Diamino-cyclohexyl)-propionamide
• CAS: 479251-84-8
• 化学式: C₉H₁₉N₃O
• 分子量: 185.269
• InChiKey: URFUFCAXXUGPLA-RNLVFQAGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.28
• 重原子数：
  13.0
• 可旋转键数：
  2.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  81.14
• 氢给体数：
  3.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  N-((1S,3R,5S)-3,5-Diamino-cyclohexyl)-propionamide 在 sodium tetrahydroborate 、 硼烷四氢呋喃络合物 作用下， 以 乙醇 为溶剂， 反应 46.0h， 生成 N,N'-bis(2-pyridylmethyl)-cis,cis-1,3,5-triaminocyclohexane
  参考文献：
  名称：

  Synthesis of 1,3,5-cis,cis-Triaminocyclohexane N-Pyridyl Derivatives as Potential Antitumor Agents

  摘要：

  Iron deprivation has been previously proven to be a promising strategy in treating tumor cells. A series of cis,cis-1,3,5-triaminocyclohexane N-pyridyl derivatives as iron-depleting antitumor agents were prepared. Cytotoxic activity of these derivatives was evaluated in the HeLa cancer cell line. Among the tested derivatives, N-ethyl-N,N',N"-tris(2-pyridylmethyl)-cis,cis-1,3,5-triaminocyclohexane (17) exhibited potent cytotoxicity against this cancer cell line. On the basis of the structure of 17, a bifunctional iron chelator 24 was designed and prepared. Bifunctional agent 24 possessing a maleimide linker that is functional for conjugation to thiolated monoclonal antibodies is a promising lead compound for development of antitumor conjugates for antibody-targeted therapies.

  DOI：

  10.1021/jo0204911
• 作为产物：
  描述：

  N,N'-bis-trityl-cis,cis-1,3,5-triaminocyclohexane 在 三乙胺 、 三氟乙酸 作用下， 以 甲醇 、 二氯甲烷 、 氯仿 为溶剂， 反应 50.17h， 生成 N-((1S,3R,5S)-3,5-Diamino-cyclohexyl)-propionamide
  参考文献：
  名称：

  Synthesis of 1,3,5-cis,cis-Triaminocyclohexane N-Pyridyl Derivatives as Potential Antitumor Agents

  摘要：

  Iron deprivation has been previously proven to be a promising strategy in treating tumor cells. A series of cis,cis-1,3,5-triaminocyclohexane N-pyridyl derivatives as iron-depleting antitumor agents were prepared. Cytotoxic activity of these derivatives was evaluated in the HeLa cancer cell line. Among the tested derivatives, N-ethyl-N,N',N"-tris(2-pyridylmethyl)-cis,cis-1,3,5-triaminocyclohexane (17) exhibited potent cytotoxicity against this cancer cell line. On the basis of the structure of 17, a bifunctional iron chelator 24 was designed and prepared. Bifunctional agent 24 possessing a maleimide linker that is functional for conjugation to thiolated monoclonal antibodies is a promising lead compound for development of antitumor conjugates for antibody-targeted therapies.

  DOI：

  10.1021/jo0204911