5,6,7-三羟基-2-甲基-4H-苯并吡喃-4-酮 | 5186-26-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 中文名称: 5,6,7-三羟基-2-甲基-4H-苯并吡喃-4-酮
• 英文名称: 5,6,7-trihydroxy-2-methylchromone
• 英文别名: 5,6,7-trihydroxy-2-methyl-chromen-4-one；5,6,7-Trihydroxy-2-methyl-chromen-4-on；5,6,7-Trihydroxy-2-methyl-chromon；5,6,7-trihydroxy-2-methyl-4H-chromen-4-one；5,6,7-trihydroxy-2-methylchromen-4-one
• CAS: 5186-26-5
• 化学式: C₁₀H₈O₅
• 分子量: 208.171
• InChiKey: HEVICQKVVHUFCP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  87
• 氢给体数：
  3
• 氢受体数：
  5

安全信息

• 海关编码：
  2914400090

反应信息

• 作为反应物：
  描述：

  5,6,7-三羟基-2-甲基-4H-苯并吡喃-4-酮 、 硫酸二甲酯 在 potassium carbonate 、 丙酮 作用下， 生成 2-methyl-5,6,7-trimethoxychromone
  参考文献：
  名称：

  Chakravorty et al., Proceedings - Indian Academy of Sciences, Section A, 1952, # 35, p. 34,41

  摘要：

  DOI：
• 作为产物：
  描述：

  5,7,8-trimethoxy-2-methyl-chromen-4-one 在 氢碘酸 、 乙酸酐 作用下， 生成 5,6,7-三羟基-2-甲基-4H-苯并吡喃-4-酮
  参考文献：
  名称：

  Chakravorty et al., Proceedings - Indian Academy of Sciences, Section A, 1952, # 35, p. 34,41

  摘要：

  DOI：

文献信息

• Importance of the B Ring and Its Substitution on the α-Glucosidase Inhibitory Activity of Baicalein, 5,6,7-Trihydroxyflavone
  作者：Hong GAO、Jun KAWABATA

  DOI：10.1271/bbb.68.1858

  日期：2004.1

  Hydroxychromones and B-ring-substituted 5,6,7-trihydroxyflavones were prepared to evaluate the contribution of the B ring of baicalein (5,6,7-trihydroxyflavone, 1) to its potent α-glucosidase inhibitory activity. Hydroxychromones, which lack 6-hydroxyl substitution, did not show any inhibitory activity, while 5,6,7-trihydroxy-2-methylchromone (5) showed high activity. Among the tested B-ring-substituted 5,6,7-trihydroxyflavones, the 4′-hydroxy-, 3′,4′-dihydroxy-, and 3′,4′,5′-trihydroxy-substituted derivatives were found to give more activity than that of 1. The methoxy-substituted derivatives, however, showed less activity than 1. The results suggest that the B ring of 1 was not essential, although advantageous to the activity; hydroxyl substitution on the B ring of 5,6,7-trihydroxyflavones was favorable to the activity, whereas methoxyl substitution was unfavorable; at least 4′-hydroxyl substitution of 5,6,7-trihydroxyflavones was required for enhanced activity, in which the number of hydroxyl groups did not take part.

  为了评估黄芩素（5,6,7-三羟基黄酮，1）的 B 环对其强效α-葡萄糖苷酶抑制活性的贡献，我们制备了羟基色酮和 B 环取代的 5,6,7- 三羟基黄酮。缺乏 6-羟基取代的羟基色酮没有显示出任何抑制活性，而 5,6,7-三羟基-2-甲基色酮（5）则显示出较高的活性。在测试的 B 环取代的 5,6,7-三羟基黄酮中，4′-羟基、3′,4′-二羟基和 3′,4′,5′-三羟基取代的衍生物的活性高于 1。结果表明，1 的 B 环虽然对活性有利，但并不是必需的；5,6,7-三羟基黄酮 B 环上的羟基取代对活性有利，而甲氧基取代则不利；5,6,7-三羟基黄酮至少需要 4′-羟基取代才能提高活性，羟基的数量与活性无关。
• 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.
• Furo-chromones and -Coumarins. IX. Reactions of Khellol Glucoside, Visnagin and Bergapten
  作者：Alexander Schönberg、Nasry Badran、Nicolas A. Starkowsky

  DOI：10.1021/ja01609a066

  日期：1955.2
• Chakravorty et al., Proceedings - Indian Academy of Sciences, Section A, 1952, # 35, p. 34,41
  作者：Chakravorty et al.

  DOI：——

  日期：——