(Z)-2-(1-naphthylmethylene)-4,6-dihydroxybenzofuran-3(2H)-one | 1613044-88-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 橙酮类黄酮
• 英文名称: (Z)-2-(1-naphthylmethylene)-4,6-dihydroxybenzofuran-3(2H)-one
• 英文别名: (2Z)-4,6-dihydroxy-2-(1-naphthylmethylene)benzofuran-3-one；(2Z)-4,6-dihydroxy-2-(naphthalen-1-ylmethylidene)-1-benzofuran-3-one
• CAS: 1613044-88-4
• 化学式: C₁₉H₁₂O₄
• 分子量: 304.302
• InChiKey: JHYKIALOYODGRE-IUXPMGMMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  23
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-氯-1-(2,4,6-三羟基苯基)乙酮 在 水 、 potassium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 反应 5.0h， 生成 (Z)-2-(1-naphthylmethylene)-4,6-dihydroxybenzofuran-3(2H)-one
  参考文献：
  名称：

  B-ring modified aurones as promising allosteric inhibitors of hepatitis C virus RNA-dependent RNA polymerase

  摘要：

  Following our recent report showing the potential of naturally occurring aurones (2-benzylidenebenzofuran-3(2H)-ones) as anti-hepatitis C virus (HCV) agents, efforts were continued in order to refine the structural requirements for the inhibitory effect on HCV RNA-dependent RNA polymerase (RdRp). In this study, we targeted the B-ring moiety of aurones with the aim to improve structural features associated with higher inhibition of the targeted polymerase. In vitro evaluation of the RdRp inhibitory activity of the 37 newly synthesized compounds pointed out that the replacement of the B-ring with an N-substituted indole moiety induced the highest inhibitory effect. Of these, compounds 31, 40 and 41 were found to be the most active (IC50 = 2.3-2.4 μM). Docking experiments performed with the most active compounds revealed that the allosteric thumb pocket I of RdRp is the binding pocket for aurone analogues.

  DOI：

  10.1016/j.ejmech.2014.04.005

文献信息

• B-ring modified aurones as promising allosteric inhibitors of hepatitis C virus RNA-dependent RNA polymerase
  作者：Amel Meguellati、Abdelhakim Ahmed-Belkacem、Wei Yi、Romain Haudecoeur、Marie Crouillère、Rozenn Brillet、Jean-Michel Pawlotsky、Ahcène Boumendjel、Marine Peuchmaur

  DOI：10.1016/j.ejmech.2014.04.005

  日期：2014.6

  Following our recent report showing the potential of naturally occurring aurones (2-benzylidenebenzofuran-3(2H)-ones) as anti-hepatitis C virus (HCV) agents, efforts were continued in order to refine the structural requirements for the inhibitory effect on HCV RNA-dependent RNA polymerase (RdRp). In this study, we targeted the B-ring moiety of aurones with the aim to improve structural features associated with higher inhibition of the targeted polymerase. In vitro evaluation of the RdRp inhibitory activity of the 37 newly synthesized compounds pointed out that the replacement of the B-ring with an N-substituted indole moiety induced the highest inhibitory effect. Of these, compounds 31, 40 and 41 were found to be the most active (IC50 = 2.3-2.4 μM). Docking experiments performed with the most active compounds revealed that the allosteric thumb pocket I of RdRp is the binding pocket for aurone analogues.