3,4-Dihydro-6-hydroxy-8-methoxy-3-methylbenz[α]anthracene-1,7,12(2H)-trione | 179949-47-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 角环素
• 英文名称: 3,4-Dihydro-6-hydroxy-8-methoxy-3-methylbenz[α]anthracene-1,7,12(2H)-trione
• 英文别名: 6-hydroxy-8-methoxy-3-methyl-1-oxo-2,4-dihydrobenzanthracen-7,12-dione；hatomarubigin A；hatomarubigin；6-hydroxy-8-methoxy-3-methyl-3,4-dihydrotetraphene-1,7,12(2H)-trione；6-hydroxy-8-methoxy-3-methyl-3,4-dihydro-2H-benzo[a]anthracene-1,7,12-trione
• CAS: 179949-47-4
• 化学式: C₂₀H₁₆O₅
• 分子量: 336.344
• InChiKey: INDHOTAYTXVPSZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  25
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  80.7
• 氢给体数：
  1
• 氢受体数：
  5

上下游信息

反应信息

• 作为反应物：
  描述：

  3,4-Dihydro-6-hydroxy-8-methoxy-3-methylbenz[α]anthracene-1,7,12(2H)-trione 在 三氯化铝 、 palladium diacetate 、 三乙胺 、 乙硫醇 作用下， 以 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 26.0h， 生成 dehydrorabelomycin
  参考文献：
  名称：

  A General Approach to Angucyclines: Synthesis of Hatomarubigin A, Rubiginone B2, Antibiotic X-1488E, 6-Hydroxytetrangulol, and Tetrangulol

  摘要：

  Hatomarubigin A was prepared in 41% yield in a single procedure from acyl naphthoquinone 15 and 5-methylcyclohexane-1,3-dione (16). The net reaction consists of Michael addition to an acyl quinone followed by intramolecular aldol condensation. Hatomarubigin A then served as a common intermediate in syntheses of the angucyclinone antibiotics rubiginone B2, antibiotic X-1488E, 6-hydroxy-tetrangulol, and tetrangulol. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(00)00869-3
• 作为产物：
  描述：

  3-acetyl-2-(2-methoxy-4-methyl-6-oxo-1-cyclohexenyl)-5-methoxy-1,4-dihydronaphthoquinone 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 反应 14.0h， 以27%的产率得到3,4-Dihydro-6-hydroxy-8-methoxy-3-methylbenz[α]anthracene-1,7,12(2H)-trione
  参考文献：
  名称：

  有角稠合芳族环系统的合成。3-脱氧雷贝霉素的合成

  摘要：

  由缺电子的萘醌21分四个步骤合成3-deoxyrabelomycin，总收率为17％。通过将5-甲基环己烷-1,3-二酮共轭添加到21中，然后进行甲基化和碱诱导的环化反应，制得有角度稠合的环系。

  DOI：

  10.1016/s0040-4039(00)79380-4

文献信息

• A concise total synthesis of brasiliquinones B and C and 3-deoxyrabelomycin
  作者：Dipakranjan Mal、Harendra Nath Roy

  DOI：10.1039/a905667j

  日期：——

  in 6–7 steps from the common precursor 18b. The key naphthalenones 6 were prepared in 5 steps from tetralone 17 in a regioselective manner. Anionic annulation of cyanophthalide 7c with 6 readily provided tetracyclic precursors 5 in excellent yields, sunlight-promoted photooxidation of which led to the synthesis of the title compounds.

  从普通前体18b的6-7个步骤就完成了巴西iliquinones B和C，2和3和3-deoxyrabelomycin 4a的合成。从四氢萘酮17以区域选择性的方式分五步​​制备关键萘二酮6。氰基邻苯二甲酸酯7c与6的阴离子环化反应很容易以优异的产率提供四环前体5，其在阳光下促进的光氧化作用导致合成标题化合物。
• Synthesis Study toward Mayamycin
  作者：Kui Wu、Meining Wang、Qizheng Yao、Ao Zhang

  DOI：10.1002/cjoc.201201084

  日期：2013.1

  Natural product mayamycin is the first example in the angucycline class featuring a C‐glycoside linkage at the C5‐position of the benz[a]anthracenone core with remarkable biological activities. We successfully synthesized the two retrosynthetic fragments, but found that the final C‐glycosylation did not occur. Alternatively, an A‐ring saturated aglycon was prepared, but the proposed C‐glycosylation

  天然产物玛雅霉素是安古霉素类中的第一个例子，在苯并[ a ]蒽环酮核心的C5位具有C-糖苷键，具有显着的生物活性。我们成功合成了两个逆合成片段，但发现最终的C糖基化没有发生。另外，还可以准备一个A环饱和糖苷配基，但建议的C-糖基化反应仍未进行。最后，使用简化的底物，随后的C糖基化顺利进行，从而减少了两环的玛雅霉素类似物。
• Kraus, George A.; Wu, Yusheng, Anales de Quimica, 1995, vol. 91, # 5-6, p. 394 - 398
  作者：Kraus, George A.、Wu, Yusheng

  DOI：——

  日期：——
• METHODS, COMPOSITIONS, AND KITS FOR THE TREATMENT OF CANCER
  申请人：Haggerty Timothy J.

  公开号：US20140335050A1

  公开（公告）日：2014-11-13

  The invention features methods, compositions, and kits for the administration of an HSP90 inhibitor, OBAA, flunarizine, aphidicolin, damnacanthal, dantrolene, or an analog thereof, alone, or in combination with, e.g., a TAA, an antigen-binding scaffold (e.g., an antibody, a soluble T cell receptor, or a chimeric receptor) specific for a TAA, a cell (e.g., a white blood cell that targets a cancer cell), and/or an IFN-β receptor agonist or an IFN-γ receptor agonist, for the treatment of cancer.
• A General Approach to Angucyclines: Synthesis of Hatomarubigin A, Rubiginone B2, Antibiotic X-1488E, 6-Hydroxytetrangulol, and Tetrangulol
  作者：Kathlyn A Parker、Qing-jie Ding

  DOI：10.1016/s0040-4020(00)00869-3

  日期：2000.12

  Hatomarubigin A was prepared in 41% yield in a single procedure from acyl naphthoquinone 15 and 5-methylcyclohexane-1,3-dione (16). The net reaction consists of Michael addition to an acyl quinone followed by intramolecular aldol condensation. Hatomarubigin A then served as a common intermediate in syntheses of the angucyclinone antibiotics rubiginone B2, antibiotic X-1488E, 6-hydroxy-tetrangulol, and tetrangulol. (C) 2000 Elsevier Science Ltd. All rights reserved.