(S)-cis-3-ethyl-1,2,3,4,6,11-hexahydro-1,3,5,12-tetrahydroxynaphthacene-6,11-quinone | 81844-85-1

• 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-ethyl-1,2,3,4,6,11-hexahydro-1,3,5,12-tetrahydroxynaphthacene-6,11-quinone
• 英文别名: (7S,9S)-9-ethyl-6,7,9,11-tetrahydroxy-8,10-dihydro-7H-tetracene-5,12-dione
• CAS: 81844-85-1
• 化学式: C₂₀H₁₈O₆
• 分子量: 354.359
• InChiKey: LLNJQZPRRRZFMP-YUNKPMOVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  26
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  115
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (S)-cis-3-ethyl-1,2,3,4,6,11-hexahydro-1,3,5,12-tetrahydroxynaphthacene-6,11-quinone 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>-9-ethyl-7,8,9,10-tetrahydro-6,9,11-trihydroxy-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
• 作为产物：
  描述：

  trans-1,2-diacetoxy-1,2-dihydrobenzocyclobutene 、 (S)-3-Ethyl-5,8-dimethoxy-1,2,3,4-tetrahydro-naphthalene-1,3-diol 生成 (S)-cis-3-ethyl-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

• 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：——
• 3,5,12-Trihydroxy-6,11-dioxonaphthacene
  申请人：F. HOFFMANN-LA ROCHE & CO. Aktiengesellschaft

  公开号：EP0106996B1

  公开（公告）日：1986-12-30
• 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.
• Total synthesis of some new 4-demethoxyanthracyclinones
  作者：Michael J. Broadhurst、Cedric H. Hassall、Gareth J. Thomas

  DOI：10.1016/s0040-4020(01)91526-1

  日期：1984.1