(7S,9S)-7-<(3'-amino-2',3',6'-trideoxy-α-L-lyxohexopyranosyl)oxy>-7,8,9,10-tetrahydro-6,9,11-trihydroxy-9-<1-(R)-hydroxyethyl>-5,12-naphthacenedione | 91738-92-0

• 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-α-L-lyxohexopyranosyl)oxy>-7,8,9,10-tetrahydro-6,9,11-trihydroxy-9-<1-(R)-hydroxyethyl>-5,12-naphthacenedione
• 英文别名: 13(R)-dihydro-4-demethoxydaunorubicin；idarubicinol；(7S,9S)-7-[(3'-amino-2',3',6'-trideoxy-α-L-lyxohexopyranosyl)oxy]-7,8,9,10-tetrahydro-6,9,11-trihydroxy-9-(1-(R)-hydroxyethyl)-5,12-naphthacenedione；4-Demethoxydaunorubicinol；(7S,9S)-7-[(2R,4S,5S,6S)-4-amino-5-hydroxy-6-methyloxan-2-yl]oxy-6,9,11-trihydroxy-9-[(1R)-1-hydroxyethyl]-8,10-dihydro-7H-tetracene-5,12-dione
• CAS: 91738-92-0
• 化学式: C₂₆H₂₉NO₉
• 分子量: 499.518
• InChiKey: KMIBSUUWQWSRQV-LIWFTHACSA-N

物化性质

• 沸点：
  727.8±60.0 °C(Predicted)
• 密度：
  1.56±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  36
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  180
• 氢给体数：
  6
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  (7S,9S)-7-<(3'-amino-2',3',6'-trideoxy-α-L-lyxohexopyranosyl)oxy>-7,8,9,10-tetrahydro-6,9,11-trihydroxy-9-<1-(R)-hydroxyethyl>-5,12-naphthacenedione 生成 (4S,5R,7'S)-6',7',11'-trihydroxy-2,2,5-trimethylspiro[1,3-dioxolane-4,9'-8,10-dihydro-7H-tetracene]-5',12'-dione
  参考文献：
  名称：

  13（R）-和13（S）-二氢-4-脱甲氧基-柔红霉素的全合成。修订4-去甲氧基柔红霉素的微生物和哺乳动物还原产物的立体化学

  摘要：

  13（S）-二氢-4-脱甲氧基柔红霉素而不是13（R）-异构体的性质对应于4-脱甲氧基金红霉素-红霉素的微生物和哺乳动物还原产物的性质。

  DOI：

  10.1016/s0040-4039(01)81761-5
• 作为产物：
  描述：

  1-chloro-2,3,6-trideoxy-4-O-p-nitrobenzoyl-3-trifluoroacetamido-L-lyxohexopyranose 在 silver trifluoromethanesulfonate 作用下， 生成 (7S,9S)-7-<(3'-amino-2',3',6'-trideoxy-α-L-lyxohexopyranosyl)oxy>-7,8,9,10-tetrahydro-6,9,11-trihydroxy-9-<1-(R)-hydroxyethyl>-5,12-naphthacenedione
  参考文献：
  名称：

  13（R）-和13（S）-二氢-4-脱甲氧基-柔红霉素的全合成。修订4-去甲氧基柔红霉素的微生物和哺乳动物还原产物的立体化学

  摘要：

  13（S）-二氢-4-脱甲氧基柔红霉素而不是13（R）-异构体的性质对应于4-脱甲氧基金红霉素-红霉素的微生物和哺乳动物还原产物的性质。

  DOI：

  10.1016/s0040-4039(01)81761-5

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.
• The total synthesis of 13(R)- and 13(S)-dihydro-4-demethoxy-daunorubicin. Revision of stereochemistry of the microbial and mammalian reduction product of 4-demethoxydaunorubicin
  作者：Michael J. Broadhurst、Cedric H. Hassall、Gareth J. Thomas

  DOI：10.1016/s0040-4039(01)81761-5

  日期：1984.1

  The properties of 13(S)-dihydro-4-demethoxydaunorubicin, rather than the 13(R)-isomer, correspond to those of the microbial and mammalian reduction product of 4-demethoxydauno-rubicin.

  13（S）-二氢-4-脱甲氧基柔红霉素而不是13（R）-异构体的性质对应于4-脱甲氧基金红霉素-红霉素的微生物和哺乳动物还原产物的性质。