7,8-二甲氧基-2-(2-甲氧基苯基)-4H-苯并吡喃-4-酮 | 6969-07-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 中文名称: 7,8-二甲氧基-2-(2-甲氧基苯基)-4H-苯并吡喃-4-酮
• 英文名称: 7,8-dimethoxy-2-(2-methoxyphenyl)-4H-chromen-4-one
• 英文别名: 7,8-dimethoxy-2-(2-methoxyphenyl)chromen-4-one
• CAS: 6969-07-9
• 化学式: C₁₈H₁₆O₅
• 分子量: 312.322
• InChiKey: SQXGVTMBPLETQL-UHFFFAOYSA-N

物化性质

• 沸点：
  497.1±45.0 °C(Predicted)
• 密度：
  1.242±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  7,8-二甲氧基-2-(2-甲氧基苯基)-4H-苯并吡喃-4-酮 在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 反应 72.0h， 以62%的产率得到7,8,2’-trihydroxyflavone
  参考文献：
  名称：

  Synthesis of 2′,3′,4′-trihydroxyflavone (2-D08), an inhibitor of protein sumoylation

  摘要：

  Protein sumoylation is a dynamic posttranslational modification involved in diverse biological processes during cellular homeostasis and development. Recently sumoylation has been shown to play a critical role in cancer, although to date there are few small molecule probes available to inhibit enzymes involved in the SUMO conjugation process. As part of a program to identify and study inhibitors of sumoylation we recently reported the discovery that 2',3',4'-trihydroxyflavone (2-D08) is a cell permeable, mechanistically unique inhibitor of protein sumoylation. The work reported herein describes an efficient synthesis of 2-D08 as well as a structurally related but inactive isomer. We also report an unanticipated Wessely-Moser rearrangement that occurs under vigorous methyl ether deprotection conditions. This rearrangement likely gave rise to 2-D08 during a deprotection step, resulting in 2-D08 appearing as a contaminant in a screening well from a commercial supplier. (C) 2014 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmcl.2014.01.010
• 作为产物：
  描述：

  6-acetyl-2,3-dimethoxyphenyl 2-methoxybenzoate 在 吡啶 、 硫酸 、 potassium hydroxide 作用下， 以 溶剂黄146 为溶剂， 反应 3.0h， 生成 7,8-二甲氧基-2-(2-甲氧基苯基)-4H-苯并吡喃-4-酮
  参考文献：
  名称：

  Synthesis of 2′,3′,4′-trihydroxyflavone (2-D08), an inhibitor of protein sumoylation

  摘要：

  Protein sumoylation is a dynamic posttranslational modification involved in diverse biological processes during cellular homeostasis and development. Recently sumoylation has been shown to play a critical role in cancer, although to date there are few small molecule probes available to inhibit enzymes involved in the SUMO conjugation process. As part of a program to identify and study inhibitors of sumoylation we recently reported the discovery that 2',3',4'-trihydroxyflavone (2-D08) is a cell permeable, mechanistically unique inhibitor of protein sumoylation. The work reported herein describes an efficient synthesis of 2-D08 as well as a structurally related but inactive isomer. We also report an unanticipated Wessely-Moser rearrangement that occurs under vigorous methyl ether deprotection conditions. This rearrangement likely gave rise to 2-D08 during a deprotection step, resulting in 2-D08 appearing as a contaminant in a screening well from a commercial supplier. (C) 2014 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmcl.2014.01.010

文献信息

• Substituted benzopyranones as telomerase inhibitors
  申请人：——

  公开号：US20020160983A1

  公开（公告）日：2002-10-31

  The present invention relates to benzopyranone derivatives, to methods for treating telomerase-modulated diseases, in particular cancers, with said derivatives, to a process for their preparation, to their use as medicaments and to pharmaceutical compositions comprising them.

  本发明涉及苯并吡喃酮衍生物，涉及使用所述衍生物治疗端粒酶调节疾病的方法，特别是癌症，涉及它们的制备过程，它们作为药物的使用，以及包含它们的药物组合物。
• SUBSTITUTED BENZOPYRANONES AS TELOMERASE INHIBITORS
  申请人：Pharmacia Italia S.p.A.

  公开号：EP1373244A2

  公开（公告）日：2004-01-02
• [EN] SUBSTITUTED BENZOPYRANONES AS TELOMERASE INHIBITORS<br/>[FR] BENZOPYRANONES SUBSTITUES UTILISES EN TANT QU'INHIBITEURS DE TELOMERASE
  申请人：PHARMACIA ITALIA SPA

  公开号：WO2002074036A2

  公开（公告）日：2002-09-26

  The present invention relates to benzopyranone derivative, to methods for treating telomerase-modulated diseases, in particular cancers, with said derivatives, to a process for their preparation, to their use as medicaments and to pharmaceutical compositions comprising them.
• Synthesis of 2′,3′,4′-trihydroxyflavone (2-D08), an inhibitor of protein sumoylation
  作者：Yeong Sang Kim、Samantha G.L. Keyser、John S. Schneekloth

  DOI：10.1016/j.bmcl.2014.01.010

  日期：2014.2

  Protein sumoylation is a dynamic posttranslational modification involved in diverse biological processes during cellular homeostasis and development. Recently sumoylation has been shown to play a critical role in cancer, although to date there are few small molecule probes available to inhibit enzymes involved in the SUMO conjugation process. As part of a program to identify and study inhibitors of sumoylation we recently reported the discovery that 2',3',4'-trihydroxyflavone (2-D08) is a cell permeable, mechanistically unique inhibitor of protein sumoylation. The work reported herein describes an efficient synthesis of 2-D08 as well as a structurally related but inactive isomer. We also report an unanticipated Wessely-Moser rearrangement that occurs under vigorous methyl ether deprotection conditions. This rearrangement likely gave rise to 2-D08 during a deprotection step, resulting in 2-D08 appearing as a contaminant in a screening well from a commercial supplier. (C) 2014 Published by Elsevier Ltd.