1-(6-hydroxy-4,7-dimethoxy-benzofuran-5-yl)-3t-phenyl-propenone | 49572-76-1

• 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: 1-(6-hydroxy-4,7-dimethoxy-benzofuran-5-yl)-3t-phenyl-propenone
• 英文别名: 1-(6-Hydroxy-4,7-dimethoxy-benzofuran-5-yl)-3t-phenyl-propenon；1-(6-Hydroxy-4,7-dimethoxybenzofuran-5-yl)-3-phenylprop-2-en-1-one；(E)-1-(6-hydroxy-4,7-dimethoxy-1-benzofuran-5-yl)-3-phenylprop-2-en-1-one
• CAS: 49572-76-1
• 化学式: C₁₉H₁₆O₅
• 分子量: 324.333
• InChiKey: YUHVWUKXIRHANR-CMDGGOBGSA-N

物化性质

• 熔点：
  129 °C
• 沸点：
  545.1±50.0 °C(Predicted)
• 密度：
  1.281±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  24
• 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：
  68.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-(6-hydroxy-4,7-dimethoxy-benzofuran-5-yl)-3t-phenyl-propenone 在 sodium hydroxide 、 双氧水 作用下， 生成 2-benzylidene-4,8-dimethoxy-benzo[1,2-b;5,4-b']difuran-3-one
  参考文献：
  名称：

  Furo-chromones and -Coumarins. VII. Degradation of Visnagin, Khellin and Related Substances; Experiments with Chromic Acid and Hydrogen Peroxide; and a Synthesis of Eugenitin

  摘要：

  DOI：

  10.1021/ja01116a032
• 作为产物：
  描述：

  凯林酮 、 苯甲醛 在 sodium hydroxide 、 柠檬酸 作用下， 以 水 、 甲醇 为溶剂， 以78%的产率得到1-(6-hydroxy-4,7-dimethoxy-benzofuran-5-yl)-3t-phenyl-propenone
  参考文献：
  名称：

  [EN] NOVEL CHALCONE DERIVATIVES AND USES THEREOF
  [FR] NOUVEAUX DERIVES DE CHALCONE ET LEURS UTILISATIONS

  摘要：

  本文介绍了通式（I）的各种香豆素衍生物，其中变量A、B、m和R1到R10的定义如规范所述。这些衍生物可用于调节细胞中的钾通道活性，并可能在治疗或预防自身免疫和炎症性疾病方面有用。

  公开号：

  WO2003076407A1

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.
• Musante, Gazzetta Chimica Italiana, 1958, vol. 88, p. 910,928
  作者：Musante

  DOI：——

  日期：——
• DOSS N. L.; AZLZ G.; SELIM S. F.; NOSSEIR M. H., EGYPT. J. CHEM., 1977 (1979), 20, NO 3, 315-321
  作者：DOSS N. L.、 AZLZ G.、 SELIM S. F.、 NOSSEIR M. H.

  DOI：——

  日期：——
• AZIR G.; NOSSEIR M. H.; DOSS N. L.; SELIM S. F., EGYPT. J. CHEM., 1976(1978), 19, NO 5, 835-850
  作者：AZIR G.、 NOSSEIR M. H.、 DOSS N. L.、 SELIM S. F.

  DOI：——

  日期：——
• NAKKADY, SALLY;EL-DIWANY, HODA;ARBID, MAHMOUD S. S.;GOHAR, ABDEL KARIM M.+, EGYPT. J. PHARM. SCI., 30,(1989) N-4, C. 351-360
  作者：NAKKADY, SALLY、EL-DIWANY, HODA、ARBID, MAHMOUD S. S.、GOHAR, ABDEL KARIM M.+

  DOI：——

  日期：——