aflaquinolone B | 1356937-42-2

• 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: aflaquinolone B
• 英文别名: (3S,4S)-4,5-dihydroxy-6-[(E)-2-[(1R,3S,4R)-4-hydroxy-1,3-dimethylcyclohexyl]ethenyl]-3-methoxy-4-phenyl-1,3-dihydroquinolin-2-one
• CAS: 1356937-42-2
• 化学式: C₂₆H₃₁NO₅
• 分子量: 437.536
• InChiKey: VHCOEFMALBJZLE-AXOBRITRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  32
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  99
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  aflaquinolone B 在 4-二甲氨基吡啶 、 potassium carbonate 、 N,N'-二环己基碳二亚胺 、 三氟乙酸 作用下， 以 二氯甲烷 、 丙酮 、 甲苯 为溶剂， 反应 59.0h， 生成
  参考文献：
  名称：

  生物碱衍生物及其作为药物的应用

  摘要：

  本发明涉及一种抗RSV活性的喹啉酮生物碱衍生物及其制备方法，具体涉及式I‑1化合物、其立体异构体、其几何异构体、其溶剂化物、其药学上可接受的盐或其盐的溶剂化物及其作为抗病毒剂的应用。本发明提供的喹啉酮生物碱衍生物具有高效、低毒的特点，具有被开发为抗病毒药物的潜力，尤其是可用于预防和/或治疗RSV感染引起的疾病。

  公开号：

  CN104945320B
• 作为产物：
  描述：

  aflaquinolone A 在 sodium tetrahydroborate 、 水 、 氯化铵 作用下， 以 甲醇 、 乙醚 为溶剂， 反应 1.0h， 生成 aflaquinolone B
  参考文献：
  名称：

  Aflaquinolones A–G: Secondary Metabolites from Marine and Fungicolous Isolates of Aspergillus spp.

  摘要：

  Seven new compounds (aflaquinolones A-G; 1-7) containing dihydroquinolin-2-one and terpenoid units have been isolated from two different fungal sources. Two of these metabolites (1 and 2) were obtained from a Hawaiian fungicolous isolate of Aspergillus sp. (section Flavipedes; MYC-2048 = NRRL 58570), while the others were obtained from a marine Aspergillus isolate (SF-5044) collected in Korea. The structures of these compounds were determined mainly by analysis of NMR and MS data. Relative and absolute configurations were assigned on the basis of NOESY data and H-1 NMR J-values, comparison of calculated and experimental ECD spectra, and analysis of a Mosher's ester derivative of 2. Several known compounds, including alantrypinone, aspochalasins I and J, methyl 3,4,5-trimethoxy-2((2-((3-pyridinylcarbonyl)amino)benzoyl)amino)benzoate, and trans-dehydrocurvularin were also encountered in the extract of the Hawaiian isolate.

  DOI：

  10.1021/np200958r

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).
• 生物碱衍生物及其作为药物的应用
  申请人：扬州蓝色生物医药科技有限公司

  公开号：CN104945320B

  公开（公告）日：2019-01-15

  本发明涉及一种抗RSV活性的喹啉酮生物碱衍生物及其制备方法，具体涉及式I‑1化合物、其立体异构体、其几何异构体、其溶剂化物、其药学上可接受的盐或其盐的溶剂化物及其作为抗病毒剂的应用。本发明提供的喹啉酮生物碱衍生物具有高效、低毒的特点，具有被开发为抗病毒药物的潜力，尤其是可用于预防和/或治疗RSV感染引起的疾病。
• Aflaquinolones A–G: Secondary Metabolites from Marine and Fungicolous Isolates of <i>Aspergillus</i> spp.
  作者：Scott A. Neff、Sang Un Lee、Yukihiro Asami、Jong Seog Ahn、Hyuncheol Oh、Jonas Baltrusaitis、James B. Gloer、Donald T. Wicklow

  DOI：10.1021/np200958r

  日期：2012.3.23

  Seven new compounds (aflaquinolones A-G; 1-7) containing dihydroquinolin-2-one and terpenoid units have been isolated from two different fungal sources. Two of these metabolites (1 and 2) were obtained from a Hawaiian fungicolous isolate of Aspergillus sp. (section Flavipedes; MYC-2048 = NRRL 58570), while the others were obtained from a marine Aspergillus isolate (SF-5044) collected in Korea. The structures of these compounds were determined mainly by analysis of NMR and MS data. Relative and absolute configurations were assigned on the basis of NOESY data and H-1 NMR J-values, comparison of calculated and experimental ECD spectra, and analysis of a Mosher's ester derivative of 2. Several known compounds, including alantrypinone, aspochalasins I and J, methyl 3,4,5-trimethoxy-2((2-((3-pyridinylcarbonyl)amino)benzoyl)amino)benzoate, and trans-dehydrocurvularin were also encountered in the extract of the Hawaiian isolate.