(S)-cis-3-<1(R)-acetoxyethyl>-1,2,3,4,6,11-hexahydro-1,3,5,12-tetrahydroxynaphthacene-6,11-quinone | 95334-89-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 并四苯
• 英文名称: (S)-cis-3-<1(R)-acetoxyethyl>-1,2,3,4,6,11-hexahydro-1,3,5,12-tetrahydroxynaphthacene-6,11-quinone
• 英文别名: (S)-cis-3-(1(R)-acetoxyethyl)-1,2,3,4,6,11-hexahydro-1,3,5,12-tetrahydroxynaphthacene-6,11-quinone；[(1R)-1-[(2S,4S)-2,4,5,12-tetrahydroxy-6,11-dioxo-3,4-dihydro-1H-tetracen-2-yl]ethyl] acetate
• CAS: 95334-89-7
• 化学式: C₂₂H₂₀O₈
• 分子量: 412.396
• InChiKey: BHGCLAUHWKHVNV-VMGOENGKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  30
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  141
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (S)-cis-3-<1(R)-acetoxyethyl>-1,2,3,4,6,11-hexahydro-1,3,5,12-tetrahydroxynaphthacene-6,11-quinone 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：

  (3'S)-1',2',3',4'-tetrahydro-3'-hydroxy-3'-(1-hydroxyethyl)-5',8'-dimethoxyspiro[1,3-dithiolane-2,1'-naphthalene] 在 sodium tetrahydroborate 、 mercury dichloride 、 mercury(II) oxide 作用下， 以 吡啶 为溶剂， 反应 18.0h， 生成 (S)-cis-3-<1(R)-acetoxyethyl>-1,2,3,4,6,11-hexahydro-1,3,5,12-tetrahydroxynaphthacene-6,11-quinone
  参考文献：
  名称：

  Total synthesis of some new 4-demethoxyanthracyclinones

  摘要：

  DOI：

  10.1016/s0040-4020(01)91526-1

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.
• 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：——