6-acetylbenzoselenazolinone | 142776-30-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 6-acetylbenzoselenazolinone
• 英文别名: 6-acetyl-3H-1,3-benzoselenazol-2-one
• CAS: 142776-30-5
• 化学式: C₉H₇NO₂Se
• 分子量: 240.12
• InChiKey: WTVXQRGAALLYHP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.79
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  46.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  6-acetylbenzoselenazolinone 在 sodium hydroxide 、 sodium tetrahydroborate 作用下， 以80%的产率得到6-(1-hydroxyethyl)-3H-1,3-benzoselenazol-2-one
  参考文献：
  名称：

  Benzoselenazolinone Derivatives Designed To Be Glutathione Peroxidase Mimetics Feature Inhibition of Cyclooxygenase/5-Lipoxygenase Pathways and Anti-inflammatory Activity

  摘要：

  Two series of compounds, substituted benzoselenazolinones and their opened analogs, diselenides, mere prepared. The diselenides were designed according to the available SAR about glutathione peroxidase mimics and were expected to have activity. An initial series of tests was performed in order to assess the glutathione peroxidase and antioxidant activity of the diselenides compared to their cyclized analogs. The diselenides were shown to be very potent (up to 3 times the activity of ebselen), whereas the benzoselenazolinones were inactive, thus confirming our hypothesis. A second series of tests was done to determine the anti-inflammatory potency of the two series. Both were found to be potent on cyclooxygenase and 5-lipoxygenase pathways (up to 95% inhibition at 10(-5) M). Some compounds were selective, and the variations in the activity allowed us to draft some structure-activity relationships. The most interesting compound of each series, 6-benzoylbenzoselenazolinone and bis[(2-amino-5-benzoyl)phenyl] diselenide, was tested in vivo on the rat foot edema induced with different phlogistic agents and was shown to have some anti-inflammatory properties.

  DOI：

  10.1021/jm00044a011
• 作为产物：
  描述：

  双(2-氨苯基)二硒 在 吡啶 、 盐酸 、 tin 、 三氯化铝 、 N,N-二甲基甲酰胺 作用下， 反应 4.5h， 生成 6-acetylbenzoselenazolinone
  参考文献：
  名称：

  Benzoselenazolinone Derivatives Designed To Be Glutathione Peroxidase Mimetics Feature Inhibition of Cyclooxygenase/5-Lipoxygenase Pathways and Anti-inflammatory Activity

  摘要：

  Two series of compounds, substituted benzoselenazolinones and their opened analogs, diselenides, mere prepared. The diselenides were designed according to the available SAR about glutathione peroxidase mimics and were expected to have activity. An initial series of tests was performed in order to assess the glutathione peroxidase and antioxidant activity of the diselenides compared to their cyclized analogs. The diselenides were shown to be very potent (up to 3 times the activity of ebselen), whereas the benzoselenazolinones were inactive, thus confirming our hypothesis. A second series of tests was done to determine the anti-inflammatory potency of the two series. Both were found to be potent on cyclooxygenase and 5-lipoxygenase pathways (up to 95% inhibition at 10(-5) M). Some compounds were selective, and the variations in the activity allowed us to draft some structure-activity relationships. The most interesting compound of each series, 6-benzoylbenzoselenazolinone and bis[(2-amino-5-benzoyl)phenyl] diselenide, was tested in vivo on the rat foot edema induced with different phlogistic agents and was shown to have some anti-inflammatory properties.

  DOI：

  10.1021/jm00044a011

文献信息

• Regioselective Acylation of Benzoselenazolinone
  作者：V. Galet、M. P. Vaccher、J. L. Bernier、J. P. Henichart、D. Lesieur

  DOI：10.1080/00397919308009820

  日期：1993.3.1

  benzoselenazolinone were performed by using successively (i) aliphatic or aromatic acids and (ii) acid chlorides in the presence of (i) polyphosphoric acid and (ii) aluminium chloride in dimethylformamide. Regioselective acylation at C6 position was demonstrated by 1H NMR using Nuclear Overhauser Effect.

  摘要 在二甲基甲酰胺中，在 (i) 多磷酸和 (ii) 氯化铝存在下，依次使用 (i) 脂肪族或芳香族酸和 (ii) 酰氯对苯并硒唑啉酮进行取代。C6 位置的区域选择性酰化通过 1H NMR 使用核 Overhauser 效应证明。
• Benzoselenazolinone Derivatives Designed To Be Glutathione Peroxidase Mimetics Feature Inhibition of Cyclooxygenase/5-Lipoxygenase Pathways and Anti-inflammatory Activity
  作者：Vincent Galet、Jean-Luc Bernier、Jean-Piere Henichart、Daniel Lesieur、Claire Abadie、Luc Rochette、Albert Lindenbaum、Jacqueline Chalas、Jean-Francois Renaud de la Faverie

  DOI：10.1021/jm00044a011

  日期：1994.9

  Two series of compounds, substituted benzoselenazolinones and their opened analogs, diselenides, mere prepared. The diselenides were designed according to the available SAR about glutathione peroxidase mimics and were expected to have activity. An initial series of tests was performed in order to assess the glutathione peroxidase and antioxidant activity of the diselenides compared to their cyclized analogs. The diselenides were shown to be very potent (up to 3 times the activity of ebselen), whereas the benzoselenazolinones were inactive, thus confirming our hypothesis. A second series of tests was done to determine the anti-inflammatory potency of the two series. Both were found to be potent on cyclooxygenase and 5-lipoxygenase pathways (up to 95% inhibition at 10(-5) M). Some compounds were selective, and the variations in the activity allowed us to draft some structure-activity relationships. The most interesting compound of each series, 6-benzoylbenzoselenazolinone and bis[(2-amino-5-benzoyl)phenyl] diselenide, was tested in vivo on the rat foot edema induced with different phlogistic agents and was shown to have some anti-inflammatory properties.