7-hydroxy-6-methyl-4-propylbenzopyran-2-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: 7-hydroxy-6-methyl-4-propylbenzopyran-2-one
• 化学式: C₁₃H₁₄O₃
• 分子量: 218.252
• InChiKey: YTFAVLPPQLXYMG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.76
• 重原子数：
  16.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  50.44
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  7-hydroxy-6-methyl-4-propylbenzopyran-2-one 在 potassium carbonate 、 potassium hydroxide 作用下， 以 乙醇 、 丙酮 为溶剂， 反应 7.0h， 生成 6,9-dimethyl-4-propyl-2H-furo[2,3-h]-1-benzopyran-2-one
  参考文献：
  名称：

  Design, synthesis and biological evaluation of novel trimethylangelicin analogues targeting nuclear factor kB (NF-kB)

  摘要：

  A series of trimethylangelicin (TMA) derivatives were designed and synthesized to overcome the unwanted effects of TMA, promising agent for treatment of inflammation-related diseases and other pathologies, such as cystic fibrosis. The new generation TMA analogues bore hindered substituents at the 4 position in order to minimize or avoid the photoreactions with DNA. Among them, the 4-isopropyl-6-ethyl derivative 23 exhibited TMA-like inhibitory activity on NF-kappa B/DNA interactions but it proved unable to photoreact with pyrimidine bases of DNA, nor to induce any other DNA damage. The isopropyl analogue 23 was proven to lack mutagenicity when assayed through Ames test and exhibited no anti proliferative activity on cystic fibrosis IB3-1 cells, displaying at the same time inhibition of the TNF-alpha induced release of the NF-kappa B regulated PDGF-B chain, IL-10, IL-15, IL-17 and IFN-gamma. Therefore compound 23 deserves further assay to determine its anti-inflammatory properties, since it lacks photoreaction properties and mutagenicity-related side effects. (C) 2018 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2018.03.080
• 作为产物：
  描述：

  4-甲基间苯二酚 、 丁酰乙酸乙酯 在 硫酸 作用下， 反应 1.0h， 以90%的产率得到7-hydroxy-6-methyl-4-propylbenzopyran-2-one
  参考文献：
  名称：

  Design, synthesis and biological evaluation of novel trimethylangelicin analogues targeting nuclear factor kB (NF-kB)

  摘要：

  A series of trimethylangelicin (TMA) derivatives were designed and synthesized to overcome the unwanted effects of TMA, promising agent for treatment of inflammation-related diseases and other pathologies, such as cystic fibrosis. The new generation TMA analogues bore hindered substituents at the 4 position in order to minimize or avoid the photoreactions with DNA. Among them, the 4-isopropyl-6-ethyl derivative 23 exhibited TMA-like inhibitory activity on NF-kappa B/DNA interactions but it proved unable to photoreact with pyrimidine bases of DNA, nor to induce any other DNA damage. The isopropyl analogue 23 was proven to lack mutagenicity when assayed through Ames test and exhibited no anti proliferative activity on cystic fibrosis IB3-1 cells, displaying at the same time inhibition of the TNF-alpha induced release of the NF-kappa B regulated PDGF-B chain, IL-10, IL-15, IL-17 and IFN-gamma. Therefore compound 23 deserves further assay to determine its anti-inflammatory properties, since it lacks photoreaction properties and mutagenicity-related side effects. (C) 2018 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2018.03.080

文献信息

• Design, synthesis and biological evaluation of novel trimethylangelicin analogues targeting nuclear factor kB (NF-kB)
  作者：Giovanni Marzaro、Ilaria Lampronti、Elisabetta D'Aversa、Gianni Sacchetti、Giorgia Miolo、Christian Vaccarin、Giulio Cabrini、Maria Cristina Dechecchi、Roberto Gambari、Adriana Chilin

  DOI：10.1016/j.ejmech.2018.03.080

  日期：2018.5

  A series of trimethylangelicin (TMA) derivatives were designed and synthesized to overcome the unwanted effects of TMA, promising agent for treatment of inflammation-related diseases and other pathologies, such as cystic fibrosis. The new generation TMA analogues bore hindered substituents at the 4 position in order to minimize or avoid the photoreactions with DNA. Among them, the 4-isopropyl-6-ethyl derivative 23 exhibited TMA-like inhibitory activity on NF-kappa B/DNA interactions but it proved unable to photoreact with pyrimidine bases of DNA, nor to induce any other DNA damage. The isopropyl analogue 23 was proven to lack mutagenicity when assayed through Ames test and exhibited no anti proliferative activity on cystic fibrosis IB3-1 cells, displaying at the same time inhibition of the TNF-alpha induced release of the NF-kappa B regulated PDGF-B chain, IL-10, IL-15, IL-17 and IFN-gamma. Therefore compound 23 deserves further assay to determine its anti-inflammatory properties, since it lacks photoreaction properties and mutagenicity-related side effects. (C) 2018 Elsevier Masson SAS. All rights reserved.