5-methyl-4-[(3-methylbut-2-enyl)oxy]-2H-chromen-2-one | 41753-51-9

• 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: 5-methyl-4-[(3-methylbut-2-enyl)oxy]-2H-chromen-2-one
• 英文别名: Gerberacumarin；5-Methyl-4-(3-methylbut-2-enoxy)chromen-2-one；5-methyl-4-(3-methylbut-2-enoxy)chromen-2-one
• CAS: 41753-51-9
• 化学式: C₁₅H₁₆O₃
• 分子量: 244.29
• InChiKey: OADKBSPQYAJHHS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  3-(3-methylphenoxy)-3-oxopropanoic acid 在 硫酸 、 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 6.0h， 生成 5-methyl-4-[(3-methylbut-2-enyl)oxy]-2H-chromen-2-one
  参考文献：
  名称：

  Synthesis and evaluation of antibacterial and anti-inflammatory properties of naturally occurring coumarins

  摘要：

  Coumarins are a group of heterocyclic compounds naturally present in a large variety of plant families. Nevertheless, oxyprenylated coumarins have been only recently seen as valuable and promising biologically active phytochemicals. In this study, we synthesized three naturally occurring O-prenylcoumarins (1), (2), and (3), and evaluated their antibacterial and anti-inflammatory properties in view of their therapeutic potential against periodontal disease. The three O-prenylcoumarins were synthesized using well-known schemes leading to the chromen-2-one nucleus. The periodontal pathogen Porphyromonas gingivalis was found to be highly susceptible to all three O-prenylcoumarins with minimal inhibitory concentration values in the range of 12.5-25 mg/ml; the non-prenylated forms of the coumarins did not show any activity. The antibacterial activity of (1), (2), and (3) appeared to result from its ability to permeate the cell membrane. Using the U937-3xkB-LUC human monocytic cell line, compounds (2) and (3) dose-dependently inhibited lipopolysaccharide-induced NF-kB activation, while (1) did not. The non-prenylated forms of the coumarins were either inactive or much less potent. In conclusion, O-prenylcoumarins (2) and (3) by exhibiting a dual mode of action including antibacterial and anti-inflammatory activities may represent promising targeted therapeutic agents for localized treatment of periodontal diseases. (C) 2015 Phytochemical Society of Europe. Published by Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.phytol.2015.08.008

文献信息

• Synthesis and evaluation of antibacterial and anti-inflammatory properties of naturally occurring coumarins
  作者：Jabrane Azelmat、Serena Fiorito、Vito Alessandro Taddeo、Salvatore Genovese、Francesco Epifano、Daniel Grenier

  DOI：10.1016/j.phytol.2015.08.008

  日期：2015.9

  Coumarins are a group of heterocyclic compounds naturally present in a large variety of plant families. Nevertheless, oxyprenylated coumarins have been only recently seen as valuable and promising biologically active phytochemicals. In this study, we synthesized three naturally occurring O-prenylcoumarins (1), (2), and (3), and evaluated their antibacterial and anti-inflammatory properties in view of their therapeutic potential against periodontal disease. The three O-prenylcoumarins were synthesized using well-known schemes leading to the chromen-2-one nucleus. The periodontal pathogen Porphyromonas gingivalis was found to be highly susceptible to all three O-prenylcoumarins with minimal inhibitory concentration values in the range of 12.5-25 mg/ml; the non-prenylated forms of the coumarins did not show any activity. The antibacterial activity of (1), (2), and (3) appeared to result from its ability to permeate the cell membrane. Using the U937-3xkB-LUC human monocytic cell line, compounds (2) and (3) dose-dependently inhibited lipopolysaccharide-induced NF-kB activation, while (1) did not. The non-prenylated forms of the coumarins were either inactive or much less potent. In conclusion, O-prenylcoumarins (2) and (3) by exhibiting a dual mode of action including antibacterial and anti-inflammatory activities may represent promising targeted therapeutic agents for localized treatment of periodontal diseases. (C) 2015 Phytochemical Society of Europe. Published by Elsevier B.V. All rights reserved.