3-(4-hydroxy-6,7-dimethyl-2-oxo-2H-chromene-3-yl)-7,8-dimethyl-2-methoxy-2,3-dihydro-4H-furo[3,2-c]chromene-4-one

• 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-6,7-dimethyl-2-oxo-2H-chromene-3-yl)-7,8-dimethyl-2-methoxy-2,3-dihydro-4H-furo[3,2-c]chromene-4-one
• 英文别名: 3-(4-Hydroxy-6,7-dimethyl-2-oxochromen-3-yl)-2-methoxy-7,8-dimethyl-2,3-dihydrofuro[3,2-c]chromen-4-one；3-(4-hydroxy-6,7-dimethyl-2-oxochromen-3-yl)-2-methoxy-7,8-dimethyl-2,3-dihydrofuro[3,2-c]chromen-4-one
• 化学式: C₂₅H₂₂O₇
• 分子量: 434.445
• InChiKey: BPTFUJWCDWRHEL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  32
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  91.3
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  3-(4-hydroxy-6,7-dimethyl-2-oxo-2H-chromene-3-yl)-7,8-dimethyl-2-methoxy-2,3-dihydro-4H-furo[3,2-c]chromene-4-one 在 溶剂黄146 作用下， 生成 2-(4-hydroxy-6,7-dimethyl-2-oxo-2H-chromene-3-yl)-7,8-dimethyl-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-6,7-二甲基香豆素 、 乙二醛-1,1-二甲基乙缩醛溶液 以 甲醇 为溶剂， 反应 5.0h， 生成 3-(4-hydroxy-6,7-dimethyl-2-oxo-2H-chromene-3-yl)-7,8-dimethyl-2-methoxy-2,3-dihydro-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

文献信息

• Substituted furochromenes, preparation thereof and their antiinflammatory action
  申请人：Mercep Mladen

  公开号：US20060148889A1

  公开（公告）日：2006-07-06

  The invention relates to novel compounds of the formula (I) including all their tautomers, to pharmaceutically acceptable salts and solvates thereof, to processes and reactive intermediates for the preparation thereof, and to processes and reactive intermediates for the preparation of the compounds of the formula (II) including all their stereoisomers and tautomers to the use of the compounds of the formula (II) as suitable precursors for the preparation of the compounds of the formula (I) as well as to use of the compounds of the formula (I) and of the compounds of the formula (II) as therapeutically active agents in the prophylaxis and treatment of asthma and other inflammatory diesases and conditions in humans.

  本发明涉及公式（I）的新化合物及其所有互变异构体，其药学上可接受的盐和溶剂化物，以及其制备的过程和反应中间体，以及公式（II）的化合物及其所有立体异构体和互变异构体的制备过程和反应中间体。本发明还涉及使用公式（II）的化合物作为制备公式（I）的合适前体，以及使用公式（I）和公式（II）的化合物作为治疗哮喘和其他人类炎症疾病和病况的治疗活性剂的用途。
• US7384975B2
  申请人：——

  公开号：US7384975B2

  公开（公告）日：2008-06-10
• Synthesis and Anti-inflammatory Activity of Novel Furochromenes
  作者：Ivaylo Jivkov Elenkov、Boška Hrvačić、Stribor Marković、Milan Mesić、Andreja Čempuh Klonkay、Lidija Lerman、Anita Filipović Sučić、Ines Vujasinović、Berislav Bošnjak、Karmen Brajša、Dinko Žiher、Nada Košutić Hulita、Ivica Malnar

  DOI：10.5562/cca2240

  日期：——

  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.