22-O-(N-Me-L-valyl)aflaquinolone B | 1638761-72-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 22-O-(N-Me-L-valyl)aflaquinolone B
• 英文别名: [(1R,2S,4R)-4-[(E)-2-[(3S,4S)-4,5-dihydroxy-3-methoxy-2-oxo-4-phenyl-1,3-dihydroquinolin-6-yl]ethenyl]-2,4-dimethylcyclohexyl] (2S)-3-methyl-2-(methylamino)butanoate
• CAS: 1638761-72-4
• 化学式: C₃₂H₄₂N₂O₆
• 分子量: 550.695
• InChiKey: HXDOHVMCRWLYFS-ORYNJQNLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  40
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  117
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  22-O-(N-Me-L-valyl)aflaquinolone B 在 水 、 碳酸氢钠 、 sodium hydroxide 作用下， 以 甲醇 、 水 为溶剂， 反应 1.0h， 生成 (S)-2-((5-((S)-1-amino-1-oxopropan-2-ylamino)-2,4-dinitrophenyl)(methyl)amino)-3-methylbutanoic acid
  参考文献：
  名称：

  Anti-Respiratory Syncytial Virus Prenylated Dihydroquinolone Derivatives from the Gorgonian-Derived Fungus Aspergillus sp. XS-20090B15

  摘要：

  Two new prenylated dihydroquinolone derivatives, 22-O-(N-Me-l-valyl)aflaquinolone B (1) and 22-O-(N-Me-l-valyl)-21-epi-aflaquinolone B (2), and two known analogues, aflaquinolones A (3) and D (or a diastereomer of D, 4), were isolated from the mycelia of a gorgonian-derived Aspergillus sp. fungus. The structures of the new compounds were elucidated by spectroscopic methods, ECD spectra, Marfey's method, and chemical conversion. Compounds 1 and 2 display an unusual esterification of N-Me-l-Val to the side-chain prenyl group. Compound 2 exhibited outstanding anti-RSV activity with an IC50 value of 42 nM, approximately 500-fold stronger than that of the positive control ribavirin (IC50 = 20 μM), and showed a comparatively higher therapeutic ratio (TC50/IC50 = 520).

  DOI：

  10.1021/np500650t

文献信息

• Anti-Respiratory Syncytial Virus Prenylated Dihydroquinolone Derivatives from the Gorgonian-Derived Fungus <i>Aspergillus</i> sp. XS-20090B15
  作者：Min Chen、Chang-Lun Shao、Hong Meng、Zhi-Gang She、Chang-Yun Wang

  DOI：10.1021/np500650t

  日期：2014.12.26

  Two new prenylated dihydroquinolone derivatives, 22-O-(N-Me-l-valyl)aflaquinolone B (1) and 22-O-(N-Me-l-valyl)-21-epi-aflaquinolone B (2), and two known analogues, aflaquinolones A (3) and D (or a diastereomer of D, 4), were isolated from the mycelia of a gorgonian-derived Aspergillus sp. fungus. The structures of the new compounds were elucidated by spectroscopic methods, ECD spectra, Marfey's method, and chemical conversion. Compounds 1 and 2 display an unusual esterification of N-Me-l-Val to the side-chain prenyl group. Compound 2 exhibited outstanding anti-RSV activity with an IC50 value of 42 nM, approximately 500-fold stronger than that of the positive control ribavirin (IC50 = 20 μM), and showed a comparatively higher therapeutic ratio (TC50/IC50 = 520).