naphthacemycin A9

• 分子结构分类: 有机化合物 - 苯类化合物 - 并四苯
• 英文名称: naphthacemycin A9
• 英文别名: 7-(2,4-dimethoxy-6-methylphenyl)-2,4-dihydroxy-9-methoxy-12,12-dimethyltetracene-5,6,11-trione
• 化学式: C₃₀H₂₆O₈
• 分子量: 514.532
• InChiKey: QGVMFERVTSOKIN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  38
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  119
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 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 、 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 77.0h， 生成 naphthacemycin A9
  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

• Total synthesis of (±)-naphthacemycin A9, possessing both antibacterial activity against methicillin-resistant Staphylococcus aureus and circumventing effect of β-lactam resistance
  作者：Tomoyasu Hirose、Yasuhiro Kojima、Hidehito Matsui、Hideaki Hanaki、Masato Iwatsuki、Kazuro Shiomi、Satoshi Ōmura、Toshiaki Sunazuka

  DOI：10.1038/ja.2016.141

  日期：2017.5

  The total synthesis of KB-3346-5A9, named naphthacemycin A9, has been accomplished by combining the Dötz reaction and Suzuki-Miyaura cross coupling as well as employing Friedel-Crafts reaction with dienone-phenol rearrangement as key steps. We also describe the preparation of the simplified tetarimycin A and naphthacemycin A analogs as a model study, which coincidentally reveal unique properties of

  KB-3346-5A 9的总合成，称为萘甲霉素A 9，是通过结合Dötz反应和Suzuki-Miyaura交叉偶联以及将Frieden-Crafts反应与二烯酮-苯酚重排作为关键步骤完成的。我们还描述了简化的他他霉素A和萘甲霉素A类似物的制备作为模型研究，该研究巧合地揭示了天然存在的萘并5-6,11（12H）-三酮骨架的独特性质。评估了合成的化合物对耐甲氧西林的金黄色葡萄球菌和耐万古霉素的肠球菌（VRE）的抗菌活性，以阐明它们的结构活性关系（SARs），其结果与先前报道的替他霉素A的SAR初步研究一致。
• Synthesis of (±)-Naphthacemycin A₉
  作者：Shuai Wang、George A. Kraus

  DOI：10.1021/acs.joc.8b02658

  日期：2018.12.21

  Naphthacemycin A(9) was synthesized in nine steps by a sequence featuring a Diels-Alder reaction of a hindered aryl butadiene and a Hauser-Kraus annulation reaction.
• 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.