3-(5-(4-hydroxy-3-methoxyphenyl)-1-phenyl-4,5-dihydro-1H-pyrazol-3-yl)chromen-2-one | 950997-27-0

• 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: 3-(5-(4-hydroxy-3-methoxyphenyl)-1-phenyl-4,5-dihydro-1H-pyrazol-3-yl)chromen-2-one
• 英文别名: 3-[3-(4-Hydroxy-3-methoxyphenyl)-2-phenyl-3,4-dihydropyrazol-5-yl]chromen-2-one；3-[3-(4-hydroxy-3-methoxyphenyl)-2-phenyl-3,4-dihydropyrazol-5-yl]chromen-2-one
• CAS: 950997-27-0
• 化学式: C₂₅H₂₀N₂O₄
• 分子量: 412.445
• InChiKey: WYDSQVYNASYHAD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  31
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  71.4
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  3-[3-(3-methoxy-4-phenylmethoxyphenyl)prop-2-enoyl]chromen-2-one 在 四氯化钛 、 溶剂黄146 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 3.0h， 生成 3-(5-(4-hydroxy-3-methoxyphenyl)-1-phenyl-4,5-dihydro-1H-pyrazol-3-yl)chromen-2-one
  参考文献：
  名称：

  Antioxidant effectiveness generated by one or two phenolic hydroxyl groups in coumarin-substituted dihydropyrazoles

  摘要：

  A cascade operation was designed to synthesize nine coumarin-substituted dihydropyrazoles with only one or two phenolic hydroxyl groups contained. Antioxidant abilities of the obtained compounds were evaluated by inhibiting 2,2'-azobis(2-amidinopropanehydrochloride) (AAPH)-, Cu2+/glutathione (GSH)-, and center dot OH-induced oxidation of DNA. It was found that less phenolic hydroxyl groups can enhance the abilities of coumarin-substituted dihydropyrazoles to protect DNA against the oxidation. Moreover, these coumarin-substituted dihydropyrazoles were employed to scavenge 2,2'-azinobis(3-ethylbenzothiazoline-6sulfonate) cationic radical (ABTS(+.)), 2,2'-dipheny1-1-picrylhydrazyl radical (DPPH), and galvinoxyl radical, respectively. It was found that double phenolic hydroxyl groups were more beneficial for enhancing the abilities of coumarin-substituted dihydropyrazoles to quench the aforementioned radicals. Therefore, dihydropyrazole linked with coumarin exhibited powerful antioxidant effectiveness even in the case of less phenolic hydroxyl groups involved. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.06.059

文献信息

• Antioxidant effectiveness generated by one or two phenolic hydroxyl groups in coumarin-substituted dihydropyrazoles
  作者：Gao-Lei Xi、Zai-Qun Liu

  DOI：10.1016/j.ejmech.2013.06.059

  日期：2013.10

  A cascade operation was designed to synthesize nine coumarin-substituted dihydropyrazoles with only one or two phenolic hydroxyl groups contained. Antioxidant abilities of the obtained compounds were evaluated by inhibiting 2,2'-azobis(2-amidinopropanehydrochloride) (AAPH)-, Cu2+/glutathione (GSH)-, and center dot OH-induced oxidation of DNA. It was found that less phenolic hydroxyl groups can enhance the abilities of coumarin-substituted dihydropyrazoles to protect DNA against the oxidation. Moreover, these coumarin-substituted dihydropyrazoles were employed to scavenge 2,2'-azinobis(3-ethylbenzothiazoline-6sulfonate) cationic radical (ABTS(+.)), 2,2'-dipheny1-1-picrylhydrazyl radical (DPPH), and galvinoxyl radical, respectively. It was found that double phenolic hydroxyl groups were more beneficial for enhancing the abilities of coumarin-substituted dihydropyrazoles to quench the aforementioned radicals. Therefore, dihydropyrazole linked with coumarin exhibited powerful antioxidant effectiveness even in the case of less phenolic hydroxyl groups involved. (C) 2013 Elsevier Masson SAS. All rights reserved.