11-amino-3-(1,2-dihydroxyethyl)-3,6-dihydroxy-10-methoxy-5,12-dioxo-1,2,3,4,5,12-hexahydrotetracen-1-yl 3-(3-cyanomorpholin-4-yl)-2,3,6-trideoxyhexopyranoside | 89164-80-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 11-amino-3-(1,2-dihydroxyethyl)-3,6-dihydroxy-10-methoxy-5,12-dioxo-1,2,3,4,5,12-hexahydrotetracen-1-yl 3-(3-cyanomorpholin-4-yl)-2,3,6-trideoxyhexopyranoside
• 英文别名: 3'-deamino-3'-(3-cyano-4-morpholinyl)-5-imino-13-dihydrodoxorubicin
• CAS: 89164-80-7；89164-81-8；92693-87-3
• 化学式: C₃₂H₃₇N₃O₁₁
• 分子量: 639.659
• InChiKey: ZFHSJTKYAYTTQZ-IBMZJRTBSA-N

物化性质

• 沸点：
  894.2±65.0 °C(Predicted)
• 密度：
  1.63±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.24
• 重原子数：
  46.0
• 可旋转键数：
  6.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  226.25
• 氢给体数：
  7.0
• 氢受体数：
  14.0

反应信息

• 作为产物：
  描述：

  3'-deamino-3'-(3-cyano-4-morpholinyl)-13-dihydrodoxorubicin 在 氨 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 27.0h， 以69%的产率得到11-amino-3-(1,2-dihydroxyethyl)-3,6-dihydroxy-10-methoxy-5,12-dioxo-1,2,3,4,5,12-hexahydrotetracen-1-yl 3-(3-cyanomorpholin-4-yl)-2,3,6-trideoxyhexopyranoside
  参考文献：
  名称：

  Intensely potent morpholinyl anthracyclines

  摘要：

  3'-Deamino-3'-(3-cyano-4-morpholinyl)doxorubicin is a new analogue that is 100 to 1000 times more potent than doxorubicin against tumors in cell culture or in mice, that is active by intraperitoneal, intravenous, or oral dosing, and that does not produce chronic myocardial lesions in mice. This analogue was encountered in studies on the reductive alkylation of doxorubicin and daunorubicin with 2,2' - oxybis [acetaldehyde], which constructs a morpholino ring incorporating the amino N. The morpholinyl nitrile byproducts are separated by virtue of their nonbasicity from the expected morpholino derivatives. The 13-dihydro and 5-imino derivatives are also described in this important new class of anthracyclines.

  DOI：

  10.1021/jm00371a014