8-(3,4-dihydro-1H-isoquinolin-2-ylmethyl)-7-hydroxychromen-2-one | 1024742-97-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: 8-(3,4-dihydro-1H-isoquinolin-2-ylmethyl)-7-hydroxychromen-2-one
• CAS: 1024742-97-9
• 化学式: C₁₉H₁₇NO₃
• 分子量: 307.349
• InChiKey: RNNOXRHIPHLBSA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  49.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  8-(3,4-dihydro-1H-isoquinolin-2-ylmethyl)-7-hydroxychromen-2-one 在 双氧水 、 碘 作用下， 以 乙醇 、 水 为溶剂， 反应 18.0h， 以85%的产率得到7a,12,13,15-tetrahydro-2H-chromeno[8',7':5,6][1,3]oxazino[2,3-a]isoquinolin-2-one
  参考文献：
  名称：

  碘/过氧化氢在室温下促进乙醇中分子内氧化 C-O 键的形成：1,3-恶嗪的绿色方法

  摘要：

  开发了 I2/H2O2 促进的各种 1-(氨基烷基)-2-萘酚或 2-(氨基烷基)苯酚的分子内 C-O 键形成反应，得到相应的 1,3-恶嗪。该反应简单、原子经济，在无金属条件下，以乙醇为溶剂，在室温下顺利进行。

  DOI：

  10.1055/s-0036-1589717
• 作为产物：
  描述：

  四氢异喹啉 、 聚合甲醛 、 7-羟基香豆素 以 乙醇 为溶剂， 以65%的产率得到8-(3,4-dihydro-1H-isoquinolin-2-ylmethyl)-7-hydroxychromen-2-one
  参考文献：
  名称：

  Activity of Mannich bases of 7-hydroxycoumarin against Flaviviridae

  摘要：

  Some Mannich bases of 7-hydroxycoumarin (2) and their simple derivatives (3 and 4) were prepared and tested against viruses containing single-stranded, positive-sense RNA genomes (ssRNA(+)). This study was directed toward Flaviviridae and, in particular, HCV surrogate viruses (BVDV, YFV). The 7-hydroxy derivatives 2 were generally devoid of activity, but when position 7 was propylated, the resulting 7-propyloxy derivatives 3 were in some cases endowed with an interesting activity against BVDV. The formation of 7-benzoyl derivatives 4 gave compounds generally lacking in activity against Flaviviridae, whereas the appearance of activity against RSV has been observed. Also some unsymmetrical methylene derivatives 5-7 (namely coumarins bridged to chromones or indoles) were found moderately active in antiviral tests. Derivatives 3 were submitted to a molecular modeling study using DNA polymerase of HCV as a target. The good correlation between calculated molecular modeling IC50 and experimental EC50 indicates that DNA polymerase is potentially involved in the inhibition of surrogate HCV viruses. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2007.11.045

文献信息

• Activity of Mannich bases of 7-hydroxycoumarin against Flaviviridae
  作者：Mauro Mazzei、Erika Nieddu、Mariangela Miele、Alessandro Balbi、Marco Ferrone、Maurizio Fermeglia、Marco T. Mazzei、Sabrina Pricl、Paolo La Colla、Fabio Marongiu、Cristina Ibba、Roberta Loddo

  DOI：10.1016/j.bmc.2007.11.045

  日期：2008.3

  Some Mannich bases of 7-hydroxycoumarin (2) and their simple derivatives (3 and 4) were prepared and tested against viruses containing single-stranded, positive-sense RNA genomes (ssRNA(+)). This study was directed toward Flaviviridae and, in particular, HCV surrogate viruses (BVDV, YFV). The 7-hydroxy derivatives 2 were generally devoid of activity, but when position 7 was propylated, the resulting 7-propyloxy derivatives 3 were in some cases endowed with an interesting activity against BVDV. The formation of 7-benzoyl derivatives 4 gave compounds generally lacking in activity against Flaviviridae, whereas the appearance of activity against RSV has been observed. Also some unsymmetrical methylene derivatives 5-7 (namely coumarins bridged to chromones or indoles) were found moderately active in antiviral tests. Derivatives 3 were submitted to a molecular modeling study using DNA polymerase of HCV as a target. The good correlation between calculated molecular modeling IC50 and experimental EC50 indicates that DNA polymerase is potentially involved in the inhibition of surrogate HCV viruses. (C) 2007 Elsevier Ltd. All rights reserved.
• Iodine/Hydrogen Peroxide Promoted Intramolecular Oxidative C–O Bond Formation in Ethanol at Room Temperature: A Green Approach to 1,3-Oxazines
  作者：Mohit Deb、Pranjal Baruah、Paran Borpatra、Prakash Saikia

  DOI：10.1055/s-0036-1589717

  日期：——

  reaction of a variety of 1-(aminoalkyl)-2-naphthols or 2-(aminoalkyl)phenols to give the corresponding 1,3-oxazines was developed. The reaction is simple, atom-economic, and proceeds smoothly at room temperature under metal-free conditions in ethanol as solvent.

  开发了 I2/H2O2 促进的各种 1-(氨基烷基)-2-萘酚或 2-(氨基烷基)苯酚的分子内 C-O 键形成反应，得到相应的 1,3-恶嗪。该反应简单、原子经济，在无金属条件下，以乙醇为溶剂，在室温下顺利进行。