3-acetoxy-5,8-dihydroxy-7-methoxy-2-methylanthracene-9,10-dione | 1372979-54-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 3-acetoxy-5,8-dihydroxy-7-methoxy-2-methylanthracene-9,10-dione
• 英文别名: (5,8-Dihydroxy-6-methoxy-3-methyl-9,10-dioxoanthracen-2-yl) acetate
• CAS: 1372979-54-8
• 化学式: C₁₈H₁₄O₇
• 分子量: 342.305
• InChiKey: VGHXDXKATCUDON-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  110
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  1,4,6-trihydroxy-2-methoxy-7-methylanthracene-9,10-dione 、 乙酸酐 在 吡啶 作用下， 以 丙酮 为溶剂， 反应 4.0h， 以9 mg的产率得到8-acetoxy-3,5-dihydroxy-7-methoxy-2-methylanthracene-9,10-dione
  参考文献：
  名称：

  Antibacterial Anthraquinone Derivatives from a Sea Anemone-Derived Fungus Nigrospora sp.

  摘要：

  Chemical investigation of a marine-derived fungus Nigrospora sp., isolated from an unidentified sea anemone, yielded two new hydroanthraquinone analogues, 4a-epi-9 alpha-methoxydihydrodeoxybostrycin (1) and 10-deoxybostrycin (2), together with seven known anthraquinone derivatives (3-9). The structures of the two new compounds were established through extensive NMR spectroscopy as well as a single-crystal X-ray diffraction analysis using Cu K alpha radiation. The antibacterial activities of compounds 1-9 and 10 acetyl derivatives (6a, 7a, 8a-8g, 9a) were evaluated in vitro. Compound 6a, the acetylated derivative of 6, exhibited promising activity against Bacillus cereus with an MIC value of 48.8 nM, which was stronger than that of the positive control ciprofloxacin (MIC = 1250 nM). Analysis of the antibacterial screening data for the metabolites and their acetyl derivatives revealed the key structural features required for this activity.

  DOI：

  10.1021/np300103w

文献信息

• Antibacterial Anthraquinone Derivatives from a Sea Anemone-Derived Fungus <i>Nigrospora</i> sp.
  作者：Kai-Lin Yang、Mei-Yan Wei、Chang-Lun Shao、Xiu-Mei Fu、Zhi-Yong Guo、Ru-Fang Xu、Cai-Juan Zheng、Zhi-Gang She、Yong-Cheng Lin、Chang-Yun Wang

  DOI：10.1021/np300103w

  日期：2012.5.25

  Chemical investigation of a marine-derived fungus Nigrospora sp., isolated from an unidentified sea anemone, yielded two new hydroanthraquinone analogues, 4a-epi-9 alpha-methoxydihydrodeoxybostrycin (1) and 10-deoxybostrycin (2), together with seven known anthraquinone derivatives (3-9). The structures of the two new compounds were established through extensive NMR spectroscopy as well as a single-crystal X-ray diffraction analysis using Cu K alpha radiation. The antibacterial activities of compounds 1-9 and 10 acetyl derivatives (6a, 7a, 8a-8g, 9a) were evaluated in vitro. Compound 6a, the acetylated derivative of 6, exhibited promising activity against Bacillus cereus with an MIC value of 48.8 nM, which was stronger than that of the positive control ciprofloxacin (MIC = 1250 nM). Analysis of the antibacterial screening data for the metabolites and their acetyl derivatives revealed the key structural features required for this activity.