(7S,9S)-7-<(3'-amino-2',3',6'-trideoxy-4'-O-methyl-α-L-lyxohexopyranosyl)oxy>-7,8,9,10-tetrahydro-6,9,11-trihydroxy-9-(hydroxymethyl)-5,12-naphthacenedione | 103444-94-6

• 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: (7S,9S)-7-<(3'-amino-2',3',6'-trideoxy-4'-O-methyl-α-L-lyxohexopyranosyl)oxy>-7,8,9,10-tetrahydro-6,9,11-trihydroxy-9-(hydroxymethyl)-5,12-naphthacenedione
• 英文别名: (7S,9S)-7-[(2R,4S,5S,6S)-4-amino-5-methoxy-6-methyloxan-2-yl]oxy-6,9,11-trihydroxy-9-(hydroxymethyl)-8,10-dihydro-7H-tetracene-5,12-dione
• CAS: 103444-94-6
• 化学式: C₂₆H₂₉NO₉
• 分子量: 499.518
• InChiKey: ZULKPJPEZLVCOR-NVKQFRDVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  36
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  169
• 氢给体数：
  5
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  (1S)-cis-3-acetoxymethyl-1,2,3,4,6,11-hexahydro-1,3,5,12-tetrahydroxy-6,11-dioxonaphthacene 在 sodium hydroxide 、 silver trifluoromethanesulfonate 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 5.0h， 生成 (7S,9S)-7-<(3'-amino-2',3',6'-trideoxy-4'-O-methyl-α-L-lyxohexopyranosyl)oxy>-7,8,9,10-tetrahydro-6,9,11-trihydroxy-9-(hydroxymethyl)-5,12-naphthacenedione
  参考文献：
  名称：

  Synthesis and antitumor activity of novel 4-demethoxyanthracyclines

  摘要：

  A versatile and efficient synthetic route to 4-demethoxyanthracyclinones has been utilized in the preparation of a number of aglycons having 9-alkyl, 9-(hydroxylalkyl), or 9-carbamoyl substituents. Silver trifluoromethanesulfonate catalyzed coupling of these aglycons with various daunosamine derivatives has yielded a series of novel anthracyclines which have been evaluated as antitumor agents. 9-Alkylanthracyclines 22, 23, 33, and 34 have higher efficacy vs L-1210 leukemia than the parent 4-demethoxydaunorubicin (21), or the natural anthracyclines daunorubicin (1) and doxorubicin (2). 9-(Hydroxyalkyl) derivatives have in most cases high efficacy but are slightly less potent than 21. 9-Methyl analogue 22 has higher efficacy vs P388 leukemia than other anthracyclines tested, while 9-(hydroxymethyl) derivative 37 retains similar efficacy to anthracyclines 1, 2, and 21 but is considerably more potent. The N-substituted 9-carbamoylanthracyclines are devoid of antitumor activity.

  DOI：

  10.1021/jm00171a010

文献信息

• Synthesis and antitumor activity of novel 4-demethoxyanthracyclines
  作者：Nigel Adams、Colin Blake、Michael J. Broadhurst、David J. Bushnell、Cedric H. Hassall、Hans R. Hartmann、Elizabeth Keech、Alan R. Stratton、Gareth J. Thomas

  DOI：10.1021/jm00171a010

  日期：1990.9

  A versatile and efficient synthetic route to 4-demethoxyanthracyclinones has been utilized in the preparation of a number of aglycons having 9-alkyl, 9-(hydroxylalkyl), or 9-carbamoyl substituents. Silver trifluoromethanesulfonate catalyzed coupling of these aglycons with various daunosamine derivatives has yielded a series of novel anthracyclines which have been evaluated as antitumor agents. 9-Alkylanthracyclines 22, 23, 33, and 34 have higher efficacy vs L-1210 leukemia than the parent 4-demethoxydaunorubicin (21), or the natural anthracyclines daunorubicin (1) and doxorubicin (2). 9-(Hydroxyalkyl) derivatives have in most cases high efficacy but are slightly less potent than 21. 9-Methyl analogue 22 has higher efficacy vs P388 leukemia than other anthracyclines tested, while 9-(hydroxymethyl) derivative 37 retains similar efficacy to anthracyclines 1, 2, and 21 but is considerably more potent. The N-substituted 9-carbamoylanthracyclines are devoid of antitumor activity.