6-hydroxy-2H-benzo[h]chromen-2-one | 24052-00-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 萘并吡喃类
• 英文名称: 6-hydroxy-2H-benzo[h]chromen-2-one
• 英文别名: 6-hydroxy-benzo[h]chromen-2-one；6-Hydroxy-7,8-benzocoumarin；6-Hydroxybenzo[h]chromen-2-one
• CAS: 24052-00-4
• 化学式: C₁₃H₈O₃
• 分子量: 212.205
• InChiKey: IACHCBJDNSYAIN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  16
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  1,4-二羟基萘 、 丙炔酸乙酯 在 zinc(II) chloride 作用下， 以 1,4-二氧六环 为溶剂， 反应 216.0h， 以26%的产率得到6-hydroxy-2H-benzo[h]chromen-2-one
  参考文献：
  名称：

  Synthesis of hydroxycoumarins and hydroxybenzo[f]- or [h]coumarins as lipid peroxidation inhibitors

  摘要：

  Substituted hydroxycoumarins and 7- or 8-hydroxybenzo[f]coumarins were prepared by the treatment of phenols and naphthalenediols, respectively, with malic acid and H2SO4 under microwave irradiation. 7-or 8-Hydroxybenzo[f] coumarins and 6-hydroxybenzo[h] coumarin were synthesized by the reaction of naphthalenediols with ethylpropiolate in the presence of ZnCl2 in refluxing dioxane. The compounds were tested in vitro for their ability: (i) to interact with 1,1-diphenyl-2-picryl-hydrazyl (DPPH) stable free radical, (ii) to inhibit lipid peroxidation, (iii) to scavenge the superoxide anion, (iv) to inhibit the activity of soybean lipoxygenase and (v) to inhibit in vivo the carrageenin-induced rat paw edema. Most of them are potent superoxide anion scavengers and inhibit in vitro lipid peroxidation. The majority of the compounds did not show high lipoxygenase inhibitory activity. No differences were observed between biological responses of hydroxycoumarins and hydroxybenzocoumarins. Compound 3i was found to present a promising antioxidant profile. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.12.098

文献信息

• Synthesis of hydroxycoumarins and hydroxybenzo[f]- or [h]coumarins as lipid peroxidation inhibitors
  作者：Theodoros Symeonidis、Michael Chamilos、Dimitra J. Hadjipavlou-Litina、Michael Kallitsakis、Konstantinos E. Litinas

  DOI：10.1016/j.bmcl.2008.12.098

  日期：2009.2

  Substituted hydroxycoumarins and 7- or 8-hydroxybenzo[f]coumarins were prepared by the treatment of phenols and naphthalenediols, respectively, with malic acid and H2SO4 under microwave irradiation. 7-or 8-Hydroxybenzo[f] coumarins and 6-hydroxybenzo[h] coumarin were synthesized by the reaction of naphthalenediols with ethylpropiolate in the presence of ZnCl2 in refluxing dioxane. The compounds were tested in vitro for their ability: (i) to interact with 1,1-diphenyl-2-picryl-hydrazyl (DPPH) stable free radical, (ii) to inhibit lipid peroxidation, (iii) to scavenge the superoxide anion, (iv) to inhibit the activity of soybean lipoxygenase and (v) to inhibit in vivo the carrageenin-induced rat paw edema. Most of them are potent superoxide anion scavengers and inhibit in vitro lipid peroxidation. The majority of the compounds did not show high lipoxygenase inhibitory activity. No differences were observed between biological responses of hydroxycoumarins and hydroxybenzocoumarins. Compound 3i was found to present a promising antioxidant profile. (C) 2008 Elsevier Ltd. All rights reserved.