3-[6-(3-chloro-benzyloxy)-5-methoxy-4-oxo-4H-chromen-2-yloxymethyl]-benzonitrile | 1349177-48-5

• 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: 3-[6-(3-chloro-benzyloxy)-5-methoxy-4-oxo-4H-chromen-2-yloxymethyl]-benzonitrile
• 英文别名: 3-[[6-[(3-Chlorophenyl)methoxy]-5-methoxy-4-oxochromen-2-yl]oxymethyl]benzonitrile
• CAS: 1349177-48-5
• 化学式: C₂₅H₁₈ClNO₅
• 分子量: 447.875
• InChiKey: OFGHGUCAVLUYJA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  32
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  77.8
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3-[6-(3-chloro-benzyloxy)-5-methoxy-4-oxo-4H-chromen-2-yloxymethyl]-benzonitrile 在 aluminum (III) chloride 、 盐酸 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 4.0h， 以51%的产率得到3-[6-(3-chloro-benzyloxy)-5-hydroxy-4-oxo-4H-chromen-2-yloxymethyl]-benzonitrile
  参考文献：
  名称：

  2,6-Bis-arylmethyloxy-5-hydroxychromones with antiviral activity against both hepatitis C virus (HCV) and SARS-associated coronavirus (SCV)

  摘要：

  In this study, as a bioisosteric alternative scaffold of the antiviral aryl diketoacids (ADKs), we used 5-hydroxychromone on which two arylmethyloxy substituents were installed. The 5-hydroxychromones (5b-5g) thus prepared showed anti-HCV activity and, depending on the aromatic substituents on the 2-arylmethyloxy moiety, some of the derivatives (5b-5f) were also active against SCV. In addition, unlike the ADKs which showed selective inhibition against the helicase activity of the SCV NTPase/helicase, the 5-hydroxychromones (5b-5f) were active against both NTPase and helicase activities of the target enzyme. Among those, 3-iodobenzyloxy-substituted derivative 5e showed the most potent activity against HCV (EC50 = 4 mu M) as well as SCV (IC50 = 4 mu M for ATPase activity, 11 mu M for helicase activity) and this might be used as a platform structure for future development of the multi-target or broad-spectrum antivirals. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.09.005
• 作为产物：
  描述：

  6-(3-chloro-benzyloxy)-5-methoxy-2-methylsulfanyl-chromen-4-one 在 sodium hydride 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 18.0h， 生成 3-[6-(3-chloro-benzyloxy)-5-methoxy-4-oxo-4H-chromen-2-yloxymethyl]-benzonitrile
  参考文献：
  名称：

  2,6-Bis-arylmethyloxy-5-hydroxychromones with antiviral activity against both hepatitis C virus (HCV) and SARS-associated coronavirus (SCV)

  摘要：

  In this study, as a bioisosteric alternative scaffold of the antiviral aryl diketoacids (ADKs), we used 5-hydroxychromone on which two arylmethyloxy substituents were installed. The 5-hydroxychromones (5b-5g) thus prepared showed anti-HCV activity and, depending on the aromatic substituents on the 2-arylmethyloxy moiety, some of the derivatives (5b-5f) were also active against SCV. In addition, unlike the ADKs which showed selective inhibition against the helicase activity of the SCV NTPase/helicase, the 5-hydroxychromones (5b-5f) were active against both NTPase and helicase activities of the target enzyme. Among those, 3-iodobenzyloxy-substituted derivative 5e showed the most potent activity against HCV (EC50 = 4 mu M) as well as SCV (IC50 = 4 mu M for ATPase activity, 11 mu M for helicase activity) and this might be used as a platform structure for future development of the multi-target or broad-spectrum antivirals. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.09.005