(Z)-2-(2,4-dihydroxybenzylidene)-4,6-dihydroxybenzofuran-3(2H)-one | 105098-40-6

• 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-(2,4-dihydroxybenzylidene)-4,6-dihydroxybenzofuran-3(2H)-one
• 英文别名: (2Z)-2-[(2,4-dihydroxyphenyl)methylene]-4,6-dihydroxy-benzofuran-3-one；(2Z)-2-[(2,4-dihydroxyphenyl)methylidene]-4,6-dihydroxy-1-benzofuran-3-one
• CAS: 105098-40-6
• 化学式: C₁₅H₁₀O₆
• 分子量: 286.241
• InChiKey: CUKVFVMCLBWRHA-DXNYSGJVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  21
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  107
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  (Z)-2-(2,4-dimethoxybenzylidene)-4,6-dimethoxybenzofuran-3(2H)-one 在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 以58%的产率得到(Z)-2-(2,4-dihydroxybenzylidene)-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

文献信息

• Investigation of Binding-Site Homology between Mushroom and Bacterial Tyrosinases by Using Aurones as Effectors
  作者：Romain Haudecoeur、Aurélie Gouron、Carole Dubois、Hélène Jamet、Mark Lightbody、Renaud Hardré、Anne Milet、Elisabetta Bergantino、Luigi Bubacco、Catherine Belle、Marius Réglier、Ahcène Boumendjel

  DOI：10.1002/cbic.201402003

  日期：2014.6.16

  A lighter future: Aurones have been identified as inhibitors of melanin biosynthesis. In this study, 24 aurones were evaluated on mushroom and bacterial tyrosinases (TyM and TyB). The compounds behaved as inhibitors, substrates, or activators of both enzymes. Our results highlight similarities and differences in behavior between TyM and TyB with the same set of molecules.

  更光明的未来： Aurones已被确定为黑色素生物合成的抑制剂。在这项研究中，对蘑菇和细菌酪氨酸酶（TyM和TyB）上的24种金质进行了评估。该化合物充当两种酶的抑制剂，底物或激活剂。我们的结果强调了在同一分子下TyM和TyB之间行为的异同。
• AURONES AS SELECTIVE PDE INHIBITORS AND THEIR USE IN NEUROLOGICAL CONDITIONS AND DISORDERS
  申请人：D/O V.K. George Annie George

  公开号：US20100267823A1

  公开（公告）日：2010-10-21

  The invention relates to aurones and extracts comprising them useful in the prophylactic and/or therapeutic treatment of an animal (including a human) with a phosphodiesterase (PDE) dependent disease or condition of the central nervous system, as well as methods, uses and other inventions related thereto.
• AURONES AS ESTROGEN RECEPTOR MODULATORS AND THEIR USE IN SEX HORMONE DEPENDENT DISEASES
  申请人：George Annie George D/O V.K.

  公开号：US20100267822A1

  公开（公告）日：2010-10-21

  The invention relates to aurones and extracts comprising them useful in the prophylactic and/or therapeutic treatment of an animal (including a human) with an estrogen receptor (ER) related disease or condition of the animal or human body, as well as methods, uses and other inventions related thereto.
• [EN] AURONES AS SELECTIVE PDE INHIBITORS AND THEIR USE IN NEUROLOGICAL CONDITIONS AND DISORDERS<br/>[FR] AURONES EN TANT QU'INHIBITEURS SÉLECTIFS DE PDE ET LEUR UTILISATION DANS DES AFFECTIONS ET TROUBLES NEUROLOGIQUES
  申请人：BIOTROPICS MALAYSIA BERHAD

  公开号：WO2010110646A1

  公开（公告）日：2010-09-30

  The invention relates to aurones and extracts comprising them useful in the prophylactic and/or therapeutic treatment of an animal (including a human) with a phosphodiesterase (PDE) dependent disease or condition of the central nervous system, as well as methods, uses and other inventions related thereto.
• [EN] AURONES AS ESTROGEN RECEPTOR MODULATORS AND THEIR USE IN SEX HORMONE DEPENDENT DISEASES<br/>[FR] AURONES EN TANT QUE MODULATEURS DE RÉCEPTEUR D'OESTROGÈNE ET LEUR UTILISATION DANS DES MALADIES DÉPENDANTES DES HORMONES SEXUELLES
  申请人：BIOTROPICS MALAYSIA BERHAD

  公开号：WO2010110647A1

  公开（公告）日：2010-09-30

  The invention relates to aurones and extracts comprising them useful in the prophylactic and/or therapeutic treatment of an animal (including a human) with an estrogen receptor (ER) related disease or condition of the animal or human body, as well as methods, uses and other inventions related thereto.