(Z)-2-(4-butylbenzylidene)-4,6-dimethoxybenzofuran-3(2H)-one

• 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-(4-butylbenzylidene)-4,6-dimethoxybenzofuran-3(2H)-one
• 英文别名: (2Z)-2-[(4-butylphenyl)methylene]-4,6-dimethoxy-benzofuran-3-one；(2Z)-2-[(4-butylphenyl)methylidene]-4,6-dimethoxy-1-benzofuran-3-one
• 化学式: C₂₁H₂₂O₄
• 分子量: 338.403
• InChiKey: KVYRVXOPOWCJFY-ODLFYWEKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (Z)-2-(4-butylbenzylidene)-4,6-dimethoxybenzofuran-3(2H)-one 在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 以52%的产率得到(Z)-2-(4-butylbenzylidene)-4,6-dihydroxybenzofuran-3(2H)-one
  参考文献：
  名称：

  Discovery of Naturally Occurring Aurones That Are Potent Allosteric Inhibitors of Hepatitis C Virus RNA-Dependent RNA Polymerase

  摘要：

  We have identified naturally occurring 2-benzylidenebenzofuran-3-ones (aurones) as new templates for non-nucleoside hepatitis C virus (HCV) RNA-dependent RNA polymerase (RdRp) inhibitors. The aurone target site, identified by site-directed mutagenesis, is located in thumb pocket I of HCV RdRp. The RdRp inhibitory activity of 42 aurones was rationally explored in an enzyme assay. Molecular docking studies were used to determine how aurones bind to HCV RdRp and to predict their range of inhibitory activity. Seven aurone derivatives were found to have potent inhibitory effects on HCV RdRp, with IC(50) below 5 mu M and excellent selectivity index (inhibition activity versus cellular cytotoxicity). The most active aurone analogue was (Z)-2-((1-butyl-1H-indo1-3-yl)methylene)-4,6-dihydroxybenzofuran-3(2H)-one (compound 51), with an IC(50) of 2.2 mu M. Their potent RdRp inhibitory activity and their low toxicity make these molecules attractive candidates as direct-acting anti-HCV agents.

  DOI：

  10.1021/jm200242p
• 作为产物：
  描述：

  2-氯-1-(2,4,6-三羟基苯基)乙酮 在 sodium methylate 、 potassium carbonate 、 potassium hydroxide 作用下， 以 甲醇 、 乙二醇二甲醚 、 水 为溶剂， 反应 4.5h， 生成 (Z)-2-(4-butylbenzylidene)-4,6-dimethoxybenzofuran-3(2H)-one
  参考文献：
  名称：

  Discovery of Naturally Occurring Aurones That Are Potent Allosteric Inhibitors of Hepatitis C Virus RNA-Dependent RNA Polymerase

  摘要：

  We have identified naturally occurring 2-benzylidenebenzofuran-3-ones (aurones) as new templates for non-nucleoside hepatitis C virus (HCV) RNA-dependent RNA polymerase (RdRp) inhibitors. The aurone target site, identified by site-directed mutagenesis, is located in thumb pocket I of HCV RdRp. The RdRp inhibitory activity of 42 aurones was rationally explored in an enzyme assay. Molecular docking studies were used to determine how aurones bind to HCV RdRp and to predict their range of inhibitory activity. Seven aurone derivatives were found to have potent inhibitory effects on HCV RdRp, with IC(50) below 5 mu M and excellent selectivity index (inhibition activity versus cellular cytotoxicity). The most active aurone analogue was (Z)-2-((1-butyl-1H-indo1-3-yl)methylene)-4,6-dihydroxybenzofuran-3(2H)-one (compound 51), with an IC(50) of 2.2 mu M. Their potent RdRp inhibitory activity and their low toxicity make these molecules attractive candidates as direct-acting anti-HCV agents.

  DOI：

  10.1021/jm200242p

文献信息

• 1-Azaaurones derived from the naturally occurring aurones as potential antimalarial drugs
  作者：Florence Souard、Sabrina Okombi、Chantal Beney、Séverine Chevalley、Alexis Valentin、Ahcène Boumendjel

  DOI：10.1016/j.bmc.2010.06.008

  日期：2010.8

  We report the synthesis and in vitro antiplasmodial activity of 35 compounds, designed as analogues of the naturally occurring aurones. Several of these analogues showed submicromolar antimalarial activity against a chloroquine-resistant strain of Plasmodium falciparum (FcB1-Columbia strain) cultured on human erythrocytes. Substitution of the intracyclic oxygen in aurones by a nitrogen atom and systematic

  我们报告了35种化合物的合成和体外抗疟原虫活性，这些化合物被设计为天然存在的金刚烷的类似物。这些类似物中的几种显示出对在人红细胞上培养的恶性疟原虫抗氯喹菌株（FcB1-Columbia菌株）的亚微摩尔抗疟活性。氮原子将金环素中的环内氧取代，并且B环上取代基的系统变化表明，有前途的铅对CQ耐药菌株表现出良好的活性。特别地，4，6-二甲氧基-4'-乙基氮杂金酮22显示出抗疟原虫效力而没有明显的毒性。该化合物家族的容易合成和相关的抗疟原虫活性有利于有希望的进一步发展的候选物。
• Method of cosmetic depigmentation care by applying at least one aurone
  申请人：Perrier Eric

  公开号：US20060228313A1

  公开（公告）日：2006-10-12

  at least one aurone or a natural or synthetic derivative of aurone, or an analogue of aurone, in which the independent phenyl ring can be substituted by a heterocycle of pyrrole, imidazole, triazole, pyridine, furan, or thiophene type, is disclosed as a cosmetic agent, or as an active substance, for the manufacture either of a cosmetic composition, or of a pharmaceutical composition, notably a dermatological composition, having a melanogenesis-inhibiting activity or a depigmenting activity, or an anti-tyrosinase activity.

  本发明公开了至少一种黄酮类化合物或黄酮的天然或合成衍生物，或黄酮的类似物，其中独立的苯环可以被吡咯、咪唑、三唑、吡啶、呋喃或噻吩类的杂环取代，作为化妆品成分或活性物质，用于制备化妆品组合物或制药组合物，特别是皮肤科组合物，具有抑制黑色素生成或脱色活性或抗酪氨酸酶活性。
• A method of cosmetic depigmentation care by applying at least one aurone
  申请人：ENGELHARD LYON

  公开号：EP1709964A2

  公开（公告）日：2006-10-11

  At least one aurone or a natural or synthetic derivative of aurone, or an analogue of aurone, in which the independent phenyl ring can be substituted by a heterocycle of pyrrole, imidazole, triazole, pyridine, furan, or thiophene type, is disclosed as a cosmetic agent, or as an active substance, for the manufacture either of a cosmetic composition, or of a pharmaceutical composition, notably a dermatological composition, having a melanogenesis-inhibiting activity or a depigmenting activity, or an anti-tyrosinase activity.

  公开了至少一种脲或脲的天然或合成衍生物，或脲的类似物，其中独立的苯基环可以被吡咯、咪唑、三唑、吡啶、呋喃或噻吩类型的杂环取代，作为化妆品剂、或活性物质，用于制造具有黑色素生成抑制活性或脱色活性或抗酪氨酸酶活性的化妆品组合物或药物组合物，特别是皮肤科组合物。
• Discovery of Naturally Occurring Aurones That Are Potent Allosteric Inhibitors of Hepatitis C Virus RNA-Dependent RNA Polymerase
  作者：Romain Haudecoeur、Abdelhakim Ahmed-Belkacem、Wei Yi、Antoine Fortuné、Rozenn Brillet、Catherine Belle、Edwige Nicolle、Coralie Pallier、Jean-Michel Pawlotsky、Ahcène Boumendjel

  DOI：10.1021/jm200242p

  日期：2011.8.11

  We have identified naturally occurring 2-benzylidenebenzofuran-3-ones (aurones) as new templates for non-nucleoside hepatitis C virus (HCV) RNA-dependent RNA polymerase (RdRp) inhibitors. The aurone target site, identified by site-directed mutagenesis, is located in thumb pocket I of HCV RdRp. The RdRp inhibitory activity of 42 aurones was rationally explored in an enzyme assay. Molecular docking studies were used to determine how aurones bind to HCV RdRp and to predict their range of inhibitory activity. Seven aurone derivatives were found to have potent inhibitory effects on HCV RdRp, with IC(50) below 5 mu M and excellent selectivity index (inhibition activity versus cellular cytotoxicity). The most active aurone analogue was (Z)-2-((1-butyl-1H-indo1-3-yl)methylene)-4,6-dihydroxybenzofuran-3(2H)-one (compound 51), with an IC(50) of 2.2 mu M. Their potent RdRp inhibitory activity and their low toxicity make these molecules attractive candidates as direct-acting anti-HCV agents.