tetarimycin A | 1414365-64-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 并四苯
• 英文名称: tetarimycin A
• 英文别名: Tetarimycin A；2,4,9-trihydroxy-7,12,12-trimethyltetracene-5,6,11-trione
• CAS: 1414365-64-2
• 化学式: C₂₁H₁₆O₆
• 分子量: 364.354
• InChiKey: XQMPGQHPYUKJDG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  27
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  112
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  tetarimycin A 、 乙酸酐 在 吡啶 作用下， 反应 3.0h， 以97%的产率得到5,5,10-trimethyl-6,11,12-trioxo-5,6,11,12-tetrahydrotetracene-1,3,8-triyl triacetate
  参考文献：
  名称：

  Total Synthesis of Tetarimycin A, (±)-Naphthacemycin A₉, and (±)-Fasamycin A: Structure–Activity Relationship Studies against Drug-Resistant Bacteria

  摘要：

  Making use of a reductive olefin coupling reaction and Michael-Dieckmann condensation as two key operations, we have completed a concise total synthesis of tetarimycin A, (+/-)-naphthacemycin A(9), and (+/-)-fasamycin A in a highly convergent and practical protocol. Synthetic procedures thus developed have also been applied to provide related analogues for structure-activity relationship studies, thereby coming to the conclusion that the free hydroxyl group at C-10 is essential for exerting inhibitory activities against a panel of Gram-positive bacteria, including drug-resistant strains VRE and MRSA.

  DOI：

  10.1021/acs.joc.8b00802
• 作为产物：
  描述：

  3,5-二甲氧基苄醇 在 2-双环己基膦-2',6'-二甲氧基联苯 、 吡啶 、 potassium cyanide 、 tris-(dibenzylideneacetone)dipalladium(0) 、 18-冠醚-6 、 palladium 10% on activated carbon 、 三甲基铝 、 三氯化硼 、 三溴化硼 、 sodium carbonate 、 lithium hexamethyldisilazane 、 三氯氧磷 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 甲苯 为溶剂， 反应 85.0h， 生成 tetarimycin A
  参考文献：
  名称：

  Total Synthesis of Tetarimycin A, (±)-Naphthacemycin A₉, and (±)-Fasamycin A: Structure–Activity Relationship Studies against Drug-Resistant Bacteria

  摘要：

  Making use of a reductive olefin coupling reaction and Michael-Dieckmann condensation as two key operations, we have completed a concise total synthesis of tetarimycin A, (+/-)-naphthacemycin A(9), and (+/-)-fasamycin A in a highly convergent and practical protocol. Synthetic procedures thus developed have also been applied to provide related analogues for structure-activity relationship studies, thereby coming to the conclusion that the free hydroxyl group at C-10 is essential for exerting inhibitory activities against a panel of Gram-positive bacteria, including drug-resistant strains VRE and MRSA.

  DOI：

  10.1021/acs.joc.8b00802

文献信息

• Studies on Antibiotics Active against Resistant Bacteria. Total Synthesis of MRSA-Active Tetarimycin A and Its Analogues
  作者：Jing-Kai Huang、Tsai-Ling Yang Lauderdale、Kak-Shan Shia

  DOI：10.1021/acs.orglett.5b02039

  日期：2015.9.4

  Making use of the Hauser-Kraus annulation as a key step, the first total synthesis of tetarimycin A has been accomplished in a highly convergent and operationally simple manner. Preliminary SAR not only validated that tetarimycin A exhibited potent activity against MRSA and VRE at a low MIC value but also identified that the hydroxyl group at C-10 was essential for antibacterial activities.
• Total Synthesis of Tetarimycin A, (±)-Naphthacemycin A₉, and (±)-Fasamycin A: Structure–Activity Relationship Studies against Drug-Resistant Bacteria
  作者：Jing-Kai Huang、Tsai-Ling Yang Lauderdale、Chun-Cheng Lin、Kak-Shan Shia

  DOI：10.1021/acs.joc.8b00802

  日期：2018.6.15

  Making use of a reductive olefin coupling reaction and Michael-Dieckmann condensation as two key operations, we have completed a concise total synthesis of tetarimycin A, (+/-)-naphthacemycin A(9), and (+/-)-fasamycin A in a highly convergent and practical protocol. Synthetic procedures thus developed have also been applied to provide related analogues for structure-activity relationship studies, thereby coming to the conclusion that the free hydroxyl group at C-10 is essential for exerting inhibitory activities against a panel of Gram-positive bacteria, including drug-resistant strains VRE and MRSA.