5-hydroxy-2-methyl-6,7-bis[(3-methylbut-2-en-1-yl)oxy]-4H-chromen-4-one | 1295300-13-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 5-hydroxy-2-methyl-6,7-bis[(3-methylbut-2-en-1-yl)oxy]-4H-chromen-4-one
• 英文别名: 5-hydroxy-2-methyl-6,7-bis(3-methylbut-2-enoxy)chromen-4-one
• CAS: 1295300-13-8
• 化学式: C₂₀H₂₄O₅
• 分子量: 344.408
• InChiKey: RDNWTIGPUQYVIH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  65
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  5,6,7-三羟基-2-甲基-4H-苯并吡喃-4-酮 、 1-溴-3-甲基-2-丁烯 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 以90%的产率得到5-hydroxy-2-methyl-6,7-bis[(3-methylbut-2-en-1-yl)oxy]-4H-chromen-4-one
  参考文献：
  名称：

  Synthesis, biological evaluation and molecular docking studies of stellatin derivatives as cyclooxygenase (COX-1, COX-2) inhibitors and anti-inflammatory agents

  摘要：

  Stellatin (4), isolated from Dysophylla stellata is a cyclooxygenase (COX) inhibitor. The present study reports the synthesis and biological evaluation of new stellatin derivatives for COX-1, COX-2 inhibitory and anti-inflammatory activities. Eight derivatives showed more pronounced COX-2 inhibition than stellatin and, 17 and 21 exhibited the highest COX-2 inhibition. They also exhibited the significant anti-inflammatory activity in TPA-induced mouse ear edema assay and their anti-inflammatory effects were more than that of stellatin and indomethacin at 0.5 mg/ear. The derivatives were further evaluated for antioxidant activity wherein 16 and 17 showed potent free radical scavenging activity against DPPH and ABTS radicals. Molecular docking study revealed the binding orientations of stellatin and its derivatives into the active sites of COX-1 and COX-2 and thereby helps to design the potent inhibitors. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.01.116

文献信息

• Synthesis, biological evaluation and molecular docking studies of stellatin derivatives as cyclooxygenase (COX-1, COX-2) inhibitors and anti-inflammatory agents
  作者：Raju Gautam、Sanjay M. Jachak、Vivek Kumar、C. Gopi Mohan

  DOI：10.1016/j.bmcl.2011.01.116

  日期：2011.3

  Stellatin (4), isolated from Dysophylla stellata is a cyclooxygenase (COX) inhibitor. The present study reports the synthesis and biological evaluation of new stellatin derivatives for COX-1, COX-2 inhibitory and anti-inflammatory activities. Eight derivatives showed more pronounced COX-2 inhibition than stellatin and, 17 and 21 exhibited the highest COX-2 inhibition. They also exhibited the significant anti-inflammatory activity in TPA-induced mouse ear edema assay and their anti-inflammatory effects were more than that of stellatin and indomethacin at 0.5 mg/ear. The derivatives were further evaluated for antioxidant activity wherein 16 and 17 showed potent free radical scavenging activity against DPPH and ABTS radicals. Molecular docking study revealed the binding orientations of stellatin and its derivatives into the active sites of COX-1 and COX-2 and thereby helps to design the potent inhibitors. (C) 2011 Elsevier Ltd. All rights reserved.