(7S,9S)-7-<(3'-amino-2',3',6'-trideoxy-α-L-lyxohexopyranosyl)oxy>-7,8,9,10-tetrahydro-6,9,11-trihydroxy-9-methyl-5,12-naphthacenedione | 81844-87-3

• 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-methyl-5,12-naphthacenedione
• 英文别名: (7S,9S)-7-[(3'-amino-2',3',6'-trideoxy-α-L-lyxohexopyranosyl)oxy]-7,8,9,10-tetrahydro-6,9,11-trihydroxy-9-methyl-5,12-naphthacenedione；(7S,9S)-7-[(2R,4S,5S,6S)-4-amino-5-hydroxy-6-methyloxan-2-yl]oxy-6,9,11-trihydroxy-9-methyl-8,10-dihydro-7H-tetracene-5,12-dione
• CAS: 81844-87-3；81844-88-4
• 化学式: C₂₅H₂₇NO₈
• 分子量: 469.491
• InChiKey: YGHVQAYXNMXMOY-MFEZQYJVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  34
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  160
• 氢给体数：
  5
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  1-chloro-2,3,6-trideoxy-4-O-p-nitrobenzoyl-3-trifluoroacetamido-L-lyxohexopyranose 在 sodium hydroxide 、 silver trifluoromethanesulfonate 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 二氯甲烷 为溶剂， 反应 5.0h， 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-methyl-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

• Neue Anthracyclinglycoside, ihre Herstellung und pharmazeutische Präparate
  申请人：F. HOFFMANN-LA ROCHE & CO. Aktiengesellschaft

  公开号：EP0044954A2

  公开（公告）日：1982-02-03

  Neue Anthracyclinglykoside der Formel worin R nieder-Alkyl oder Carboxy oder eine Gruppe der Formel darstellt, wobei n 1 oder 2, Y Wasserstoff oder Alkyl und Ry und Rz jeweils Wasserstoff oder einer der Reste RY und Rz Wasserstoff und der andere Hydroxy bedeuten, erhält man durch Umsetzung der Aglykone mit einem entsprechenden halogenierten Zuckerderivat, dessen Amino-und gegebenenfalls vorhandene Hydroxygruppe geschützt sind, und anschliessender Abspaltung der Schutzgruppen. Die Verbindungen sind als Antibiotica und gegen Tumore wirksam.

  式中的新型蒽环苷 其中 R 是低级烷基或羧基或式中的基团 其中 n 为 1 或 2，Y 为氢或烷基，Ry 和 Rz 均为氢或 RY 和 Rz 自由基之一为氢，另一个为羟基。这些化合物具有抗生素和抗肿瘤的功效。
• US4591636A
  申请人：——

  公开号：US4591636A

  公开（公告）日：1986-05-27
• 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.