N,N-bis(cyanomethyl)doxorubicin | 103620-78-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 蒽环类药物
• 英文名称: N,N-bis(cyanomethyl)doxorubicin
• CAS: 103620-78-6
• 化学式: C₃₁H₃₁N₃O₁₁
• 分子量: 621.601
• InChiKey: OWXZLHJJRYQKDZ-PUCKCBAPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.39
• 重原子数：
  45.0
• 可旋转键数：
  8.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  230.87
• 氢给体数：
  5.0
• 氢受体数：
  14.0

反应信息

• 作为产物：
  描述：

  盐酸多柔比星 在 盐酸 作用下， 以 甲醇 、 氯仿 、 水 、 乙腈 为溶剂， 反应 18.0h， 生成 N,N-bis(cyanomethyl)doxorubicin
  参考文献：
  名称：

  N-(Cyanomethyl)- and N-(2-methoxy-1-cyanoethyl)anthracyclines and related carboxyl derivatives

  摘要：

  Treatment of doxorubicin with formaldehyde and NaCN afforded the N-(cyanomethyl) derivative as a stable alpha-cyanoamine with but moderate antitumor activity in mice, although it was prototypal to the intensely potent alpha-cyanomorpholine derivative. 2-Methoxyacetaldehyde and NaCN afforded the N-(2-methoxy-1-cyanoethyl) derivative as an open-chain analogue of the cyanomorpholine. This analogue underwent rapid hydrolysis to doxorubicin and appeared to act as a prodrug, giving increased antitumor efficacy although with decreased potency. N-(Carboxymethyl)daunorubicin was a highly water-soluble but inactive analogue, synthesized by N-alkylation with ethyl iodoacetate and saponification. The similar N-alkylation of N-(cyanomethyl) daunorubicin demonstrated the combining of N-alkyl chains having different functional substituents.

  DOI：

  10.1021/jm00160a047