N,N'-bis-trityl-cis,cis-1,3,5-triaminocyclohexane | 479251-79-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: N,N'-bis-trityl-cis,cis-1,3,5-triaminocyclohexane
• CAS: 479251-79-1
• 化学式: C₄₄H₄₃N₃
• 分子量: 613.846
• InChiKey: JKFZFCMINVDARD-CFPDXYPDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.4
• 重原子数：
  47.0
• 可旋转键数：
  10.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  50.08
• 氢给体数：
  3.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  N,N'-bis-trityl-cis,cis-1,3,5-triaminocyclohexane 在 盐酸 、 sodium tetrahydroborate 、 potassium carbonate 、 三氟乙酸 作用下， 以 甲醇 、 乙醇 、 氯仿 、 乙腈 、 苯 为溶剂， 反应 153.0h， 生成 N-(4-aminobutyl)-N, N',N''-tris(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：

  cis,cis-1,3,5-triaminocyclohexane 、 三苯基氯甲烷 以 氯仿 为溶剂， 反应 2.0h， 以52%的产率得到N,N'-bis-trityl-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