3-(4-hydroxy-2-oxo-2H-benzo[g]chromene-3-yl)-2-methoxy-2,3-dihydro-4H-benzo[g]furo[3,2-c]chromene-4-one | 1256614-42-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: 3-(4-hydroxy-2-oxo-2H-benzo[g]chromene-3-yl)-2-methoxy-2,3-dihydro-4H-benzo[g]furo[3,2-c]chromene-4-one
• CAS: 1256614-42-2
• 化学式: C₂₁H₁₄O₇
• 分子量: 378.338
• InChiKey: XYSSGAHOHACADI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  28.0
• 可旋转键数：
  2.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  99.11
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  3-(4-hydroxy-2-oxo-2H-benzo[g]chromene-3-yl)-2-methoxy-2,3-dihydro-4H-benzo[g]furo[3,2-c]chromene-4-one 在 溶剂黄146 作用下， 以45%的产率得到2-(4-hydroxy-2-oxo-2H-chromene-3-yl)-4H-furo[3,2-c]chromene-4-one
  参考文献：
  名称：

  Synthesis and Anti-inflammatory Activity of Novel Furochromenes

  摘要：

  A series of variously substituted furochromenes, hemiacetals 2, acetals 3, and rearranged compounds 4, were synthesized from variously substituted 4-hydroxycoumarins and evaluated in several in vitro assays, inhibition of mast cell degranulation induced by the activation of FCE receptor type I or calcium ionophore and leukotriene B-4 (LTB4) inhibition. The most active derivatives, 3p and 4p (8-iso-propyl substitution in coumarin ring) and 3r (5-methyl-8-chloro substitution), showed significant inhibition of mast cell degranulation (Fc epsilon-triggered) and LTB4, and exhibited significant local anti-inflammatory activity in PMA induced ear edema in CD1 mice, with potency equal (compounds 3p and 4p) or better (compound 3r) in comparison with zileuton, a reference drug used. It might be a promising direction for developing novel drugs as potential agents for the treatment of allergies and other inflammatory diseases.

  DOI：

  10.5562/cca2240
• 作为产物：
  描述：

  4-羟基香豆素 、 乙二醛-1,1-二甲基乙缩醛溶液 以 甲醇 为溶剂， 反应 5.0h， 以80%的产率得到3-(4-hydroxy-2-oxo-2H-benzo[g]chromene-3-yl)-2-methoxy-2,3-dihydro-4H-benzo[g]furo[3,2-c]chromene-4-one
  参考文献：
  名称：

  Synthesis and Anti-inflammatory Activity of Novel Furochromenes

  摘要：

  A series of variously substituted furochromenes, hemiacetals 2, acetals 3, and rearranged compounds 4, were synthesized from variously substituted 4-hydroxycoumarins and evaluated in several in vitro assays, inhibition of mast cell degranulation induced by the activation of FCE receptor type I or calcium ionophore and leukotriene B-4 (LTB4) inhibition. The most active derivatives, 3p and 4p (8-iso-propyl substitution in coumarin ring) and 3r (5-methyl-8-chloro substitution), showed significant inhibition of mast cell degranulation (Fc epsilon-triggered) and LTB4, and exhibited significant local anti-inflammatory activity in PMA induced ear edema in CD1 mice, with potency equal (compounds 3p and 4p) or better (compound 3r) in comparison with zileuton, a reference drug used. It might be a promising direction for developing novel drugs as potential agents for the treatment of allergies and other inflammatory diseases.

  DOI：

  10.5562/cca2240