1,3-benzoselenazolin-2-one | 142776-63-4

• 分子结构分类: 有机化合物 - 苯类化合物
• 英文名称: 1,3-benzoselenazolin-2-one
• 英文别名: 1,3-benzoselenazolinone；benzo[d][1,3]selenazol-2(3H)-one；3H-benzoselenazol-2-one；3H-Benzoselenazol-2-on；3H-1,3-benzoselenazol-2-one
• CAS: 142776-63-4
• 化学式: C₇H₅NOSe
• 分子量: 198.083
• InChiKey: FIMZRONFOHRQKE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.59
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1,3-benzoselenazolin-2-one 在 PPA 、 Polyphosphoric acid (PPA) 、 sodium ethanolate 作用下， 反应 3.0h， 生成 6-Benzoyl-3-methyl-1,3-benzoselenazol-2-one
  参考文献：
  名称：

  苯并硒唑啉酮的区域选择性酰化

  摘要：

  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。

  DOI：

  10.1080/00397919308009820
• 作为产物：
  描述：

  双(2-氨苯基)二硒 在 吡啶 、 盐酸 、 tin 作用下， 生成 1,3-benzoselenazolin-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

文献信息

• Bio‐Inspired Deaminative Hydroxylation of Aminoheterocycles and Electron‐Deficient Anilines
  作者：Clément Ghiazza、Lucas Wagner、Sergio Fernández、Markus Leutzsch、Josep Cornella

  DOI：10.1002/anie.202212219

  日期：2023.1.9

  Herein, we report a user friendly, scalable and safe procedure to convert aminoheterocycles to their hydroxylated analogues with a pyrylium tetrafluoroborate salt in combination with a hydroxamic acid. The protocol is characterized by a broad functional group tolerance, permitting the selective modification of biorelevant molecules. Mechanistic experiments allowed the identification of key intermediates

  在此，我们报告了一种用户友好、可扩展且安全的程序，使用四氟硼酸吡啶盐和异羟肟酸将氨基杂环化合物转化为其羟基化类似物。该协议的特点是具有广泛的官能团耐受性，允许对生物相关分子进行选择性修饰。机械实验允许识别整个转化过程中涉及的关键中间体。
• 414. The unsaturation and tautomeric mobility of heterocyclic compounds. Part VII. Selenazole derivatives
  作者：Chiragh Hasan、Robert F. Hunter

  DOI：10.1039/jr9350001762

  日期：——
• 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.
• 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。