(E)-1-(6-hydroxy-4,7-dimethoxy-1-benzofuran-5-yl)-3-(4-hydroxyphenyl)prop-2-en-1-one | 49572-80-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: (E)-1-(6-hydroxy-4,7-dimethoxy-1-benzofuran-5-yl)-3-(4-hydroxyphenyl)prop-2-en-1-one
• CAS: 49572-80-7
• 化学式: C₁₉H₁₆O₆
• 分子量: 340.332
• InChiKey: RCAOTKBBCGXXAD-VMPITWQZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  89.1
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (E)-1-(6-hydroxy-4,7-dimethoxy-1-benzofuran-5-yl)-3-(4-hydroxyphenyl)prop-2-en-1-one 以40%的产率得到
  参考文献：
  名称：

  HISHMAT O. H.; EL EBRASHI N. M. A., INDIAN J. CHEM. , 1974, 12, NO 10, 1052-1055

  摘要：

  DOI：
• 作为产物：
  描述：

  凯林酮 、 对羟基苯甲醛 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 反应 16.0h， 生成 (E)-1-(6-hydroxy-4,7-dimethoxy-1-benzofuran-5-yl)-3-(4-hydroxyphenyl)prop-2-en-1-one
  参考文献：
  名称：

  Khellinone Derivatives as Blockers of the Voltage-Gated Potassium Channel Kv1.3:  Synthesis and Immunosuppressive Activity

  摘要：

  The voltage-gated potassium channel Kv1.3 constitutes a promising new target for the treatment of T-cell-mediated autoimmune diseases such as multiple sclerosis. In this study, we report the discovery of two new classes of Kv1.3 blockers based on the naturally occurring compound khellinone, 5-acetyl-4,7-dimethoxy-6-hydroxybeiizofuran: (1) khellinone dimers linked via the alkylation of the 6-hydroxy groups and (2) chalcone derivatives of khellinone formed by Claisen-Schmidt condensation of the 5-acetyl group with aryl aldehydes. In particular, the chalcone 3-(4,7-dimethoxy-6-hydroxybenzofuran-5-yl)-1-phenyl-3-oxopropene (16) and several of its derivatives inhibited Kv1.3 with K-d values of 300-800 nM and a Hill coefficient of 2, displayed moderate selectivity over other Kv1-family K+ channels, suppressed T-lymphocyte proliferation at submicromolar concentrations, and showed no signs of acute toxicity in mice. Because of their relatively low molecular weight and lipophilicity and their high affinity to Kv1.3, aryl-substituted khellinone derivatives represent attractive lead compounds for the development of more potent and selective Kv1.3 blocking immunosuppressants.

  DOI：

  10.1021/jm030523s

文献信息

• Khellinone Derivatives as Blockers of the Voltage-Gated Potassium Channel Kv1.3:  Synthesis and Immunosuppressive Activity
  作者：Jonathan B. Baell、Robert W. Gable、Andrew J. Harvey、Nathan Toovey、Tanja Herzog、Wolfram Hänsel、Heike Wulff

  DOI：10.1021/jm030523s

  日期：2004.4.1

  The voltage-gated potassium channel Kv1.3 constitutes a promising new target for the treatment of T-cell-mediated autoimmune diseases such as multiple sclerosis. In this study, we report the discovery of two new classes of Kv1.3 blockers based on the naturally occurring compound khellinone, 5-acetyl-4,7-dimethoxy-6-hydroxybeiizofuran: (1) khellinone dimers linked via the alkylation of the 6-hydroxy groups and (2) chalcone derivatives of khellinone formed by Claisen-Schmidt condensation of the 5-acetyl group with aryl aldehydes. In particular, the chalcone 3-(4,7-dimethoxy-6-hydroxybenzofuran-5-yl)-1-phenyl-3-oxopropene (16) and several of its derivatives inhibited Kv1.3 with K-d values of 300-800 nM and a Hill coefficient of 2, displayed moderate selectivity over other Kv1-family K+ channels, suppressed T-lymphocyte proliferation at submicromolar concentrations, and showed no signs of acute toxicity in mice. Because of their relatively low molecular weight and lipophilicity and their high affinity to Kv1.3, aryl-substituted khellinone derivatives represent attractive lead compounds for the development of more potent and selective Kv1.3 blocking immunosuppressants.
• HISHMAT O. H.; EL EBRASHI N. M. A., INDIAN J. CHEM. <IJOC-AP>, 1974, 12, NO 10, 1052-1055
  作者：HISHMAT O. H.、 EL EBRASHI N. M. A.

  DOI：——

  日期：——