(7S,9S)-9--7,8,9,10-tetrahydro-6,7,9,11-tetrahydroxy-5,12-naphthacenedione | 128496-46-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 并四苯
• 英文名称: (7S,9S)-9--7,8,9,10-tetrahydro-6,7,9,11-tetrahydroxy-5,12-naphthacenedione
• 英文别名: (7S,9S)-9-[N-(benzyloxy)carbamoyl]-7,8,9,10-tetrahydro-6,7,9,11-tetrahydroxy-5,12-naphthacenedione；(2S,4S)-2,4,5,12-tetrahydroxy-6,11-dioxo-N-phenylmethoxy-3,4-dihydro-1H-tetracene-2-carboxamide
• CAS: 128496-46-8
• 化学式: C₂₆H₂₁NO₈
• 分子量: 475.455
• InChiKey: ZFKWAJYGNABIAK-QLXKLKPCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.83
• 重原子数：
  35.0
• 可旋转键数：
  4.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  153.39
• 氢给体数：
  5.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  (7S,9S)-9--7,8,9,10-tetrahydro-6,7,9,11-tetrahydroxy-5,12-naphthacenedione 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 4.0h， 生成 (2S,4S)-2,5,12-Trihydroxy-4-[(2R,4S,5S,6S)-5-hydroxy-6-methyl-4-(2,2,2-trifluoro-acetylamino)-tetrahydro-pyran-2-yloxy]-6,11-dioxo-1,2,3,4,6,11-hexahydro-naphthacene-2-carboxylic acid benzyloxy-amide
  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
• 作为产物：
  描述：

  O-苄基羟胺 、 Vzelaykfeyrdmf-qlxklkpcsa- 生成 (7S,9S)-9--7,8,9,10-tetrahydro-6,7,9,11-tetrahydroxy-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

• ADAMS, NIGEL;BLAKE, COLIN;BROADHURST, MICHAEL J.;BUSHNELL, DAVID J.;HASSA+, J. MED. CHEM., 33,(1990) N, C. 2375-2379
  作者：ADAMS, NIGEL、BLAKE, COLIN、BROADHURST, MICHAEL J.、BUSHNELL, DAVID J.、HASSA+

  DOI：——

  日期：——