N-(1-cyano-2-methoxyethyl)daunorubicin | 103450-89-1

• 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-(1-cyano-2-methoxyethyl)daunorubicin
• 英文别名: 2-[[(2S,3S,4S,6R)-6-[[(1S,3S)-3-acetyl-3,5,12-trihydroxy-10-methoxy-6,11-dioxo-2,4-dihydro-1H-tetracen-1-yl]oxy]-3-hydroxy-2-methyloxan-4-yl]amino]-3-methoxypropanenitrile
• CAS: 103450-89-1；103667-18-1；103667-19-2
• 化学式: C₃₁H₃₄N₂O₁₁
• 分子量: 610.618
• InChiKey: SVWBTAJDVDRINX-PZJYARSSSA-N

物化性质

• 沸点：
  865.8±65.0 °C(Predicted)
• 密度：
  1.49±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  44
• 可旋转键数：
  8
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  205
• 氢给体数：
  5
• 氢受体数：
  13

反应信息

• 作为产物：
  描述：

  道诺霉素 、 1,1,2-三甲氧基乙烷 生成 N-(1-cyano-2-methoxyethyl)daunorubicin
  参考文献：
  名称：

  摘要：

  DOI：

文献信息

• N-(Cyanomethyl)- and N-(2-methoxy-1-cyanoethyl)anthracyclines and related carboxyl derivatives
  作者：Edward M. Acton、George L. Tong、Dorris L. Taylor、David G. Streeter、Joyce A. Filppi、Richard L. Wolgemuth

  DOI：10.1021/jm00160a047

  日期：1986.10

  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.
• ——
  作者：ACTON E. M.、 TONG G. L.

  DOI：——

  日期：——