N-(2-hydroxyethyl)doxorubicin

• 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-(2-hydroxyethyl)doxorubicin
• 英文别名: (7S,9S)-6,9,11-trihydroxy-9-(2-hydroxyacetyl)-7-[(2R,4S,5S,6S)-5-hydroxy-4-(2-hydroxyethylamino)-6-methyloxan-2-yl]oxy-4-methoxy-8,10-dihydro-7H-tetracene-5,12-dione
• 化学式: C₂₉H₃₃NO₁₂
• 分子量: 587.581
• InChiKey: XZJOMGCCXRRFJX-KYZOVJJKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  42
• 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：
  212
• 氢给体数：
  7
• 氢受体数：
  13

反应信息

• 作为产物：
  描述：

  盐酸多柔比星 、 羟乙醛 在 sodium cyanoborohydride 作用下， 以 水 、 乙腈 为溶剂， 反应 1.0h， 生成 N,N-bis(2-hydroxyethyl)doxorubicin 、 N-(2-hydroxyethyl)-N,4'-O-(2-hydroxyethylidene)doxorubicin 、 N-(2-hydroxyethyl)doxorubicin
  参考文献：
  名称：

  N-(2-Hydroxyethyl)doxorubicin from hydrolysis of 3'-deamino-3'-(3-cyano-4-morpholinyl)doxorubicin

  摘要：

  The susceptibility of 3'-deamino-3'-(3-cyano-4-morpholinyl)doxorubicin to hydrolysis at pH 7, 4, and 2 has been compared with that of the typically stable morpholine analogue. At pH 7, 74% of the cyanomorpholine was unchanged after 24 h at room temperature, but at pH 2 only 10% remained. Products identified were aglycon (8%) and N-(2-hydroxyethyl)doxorubicin (7%). Most of the losses were to unidentified polar products not eluted from HPLC. Authentic hydroxyethyl was synthesized from doxorubicin by reductive alkylation with glycolaldehyde. Antitumor potency was comparable to that of doxorubicin rather than of cyanomorpholine.

  DOI：

  10.1021/jm00160a057

文献信息

• N-(2-Hydroxyethyl)doxorubicin from hydrolysis of 3'-deamino-3'-(3-cyano-4-morpholinyl)doxorubicin
  作者：Edward M. Acton、George L. Tong、Thomas H. Smith、Dorris L. Taylor、David G. Streeter、John H. Peters、G. Ross Gordon、Joyce A. Filppi、Richard L. Wolgemuth

  DOI：10.1021/jm00160a057

  日期：1986.10

  The susceptibility of 3'-deamino-3'-(3-cyano-4-morpholinyl)doxorubicin to hydrolysis at pH 7, 4, and 2 has been compared with that of the typically stable morpholine analogue. At pH 7, 74% of the cyanomorpholine was unchanged after 24 h at room temperature, but at pH 2 only 10% remained. Products identified were aglycon (8%) and N-(2-hydroxyethyl)doxorubicin (7%). Most of the losses were to unidentified polar products not eluted from HPLC. Authentic hydroxyethyl was synthesized from doxorubicin by reductive alkylation with glycolaldehyde. Antitumor potency was comparable to that of doxorubicin rather than of cyanomorpholine.