2-Benzoylamino-4h-3,1-benzoxazin-4-one | 163682-94-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并恶嗪类
• 英文名称: 2-Benzoylamino-4h-3,1-benzoxazin-4-one
• 英文别名: N-(4-oxo-3,1-benzoxazin-2-yl)benzamide
• CAS: 163682-94-8
• 化学式: C₁₅H₁₀N₂O₃
• 分子量: 266.256
• InChiKey: DXVRPRMZEWDEFU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  67.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-Benzoylamino-4h-3,1-benzoxazin-4-one 在 3-(cyclohexylamino)propanesulfonic acid buffer 、 水 作用下， 以 乙腈 为溶剂， 生成 2-(3-苯甲酰脲基)苯甲酸
  参考文献：
  名称：

  3,1-Benzothiazin-4-ones and 3,1-Benzoxazin-4-ones: Highly Different Activities in Chymotrypsin Inactivation

  摘要：

  3,1-Benzothiazin-4-ones are suIfur analogs of the potent serine protease inactivators of the 3, l-benzoxazin-4-one type, which acylate the serine residue within the active site of the enzymes. A series of 2-amino-3,1-benzothiazinones was synthesized, but these compounds showed only very little inhibitory activity toward chymotrypsin, a model serine protease. Detailed investigations revealed that benzothiazinones and benzoxazinones react with identical mechanisms, but benzothiazinones acylate chymotrypsin with much lower rate constants. Investigations of nonenzymatic hydrolysis showed the benzothiazinones to be intrinsically more stable than benzoxazinones. It was concluded from spectroscopic results, that benzoxazinones are highly activated due to the absence of ester-like resonance. 2-Benzoylamino-4H-3,1-benzoxazin-4-one was found to be a new, highly active chymotrypsin inactivator. In contrast, benzothiazinones were found to be resonance stabilized. The contribution of a resonance structure with an exocyclic oxanion to the overall structure of the benzothiazinones and its nonproductive binding to the active site explained their low reactivity toward chymotrypsin. (C) 1995 Academic Press, Inc.

  DOI：

  10.1006/bioo.1995.1006
• 作为产物：
  描述：

  苯甲酸酐 、 2-氨基-4H-苯并[d][1,3]噁嗪-4-酮 以 甲苯 为溶剂， 反应 0.5h， 以35%的产率得到2-Benzoylamino-4h-3,1-benzoxazin-4-one
  参考文献：
  名称：

  3,1-Benzothiazin-4-ones and 3,1-Benzoxazin-4-ones: Highly Different Activities in Chymotrypsin Inactivation

  摘要：

  3,1-Benzothiazin-4-ones are suIfur analogs of the potent serine protease inactivators of the 3, l-benzoxazin-4-one type, which acylate the serine residue within the active site of the enzymes. A series of 2-amino-3,1-benzothiazinones was synthesized, but these compounds showed only very little inhibitory activity toward chymotrypsin, a model serine protease. Detailed investigations revealed that benzothiazinones and benzoxazinones react with identical mechanisms, but benzothiazinones acylate chymotrypsin with much lower rate constants. Investigations of nonenzymatic hydrolysis showed the benzothiazinones to be intrinsically more stable than benzoxazinones. It was concluded from spectroscopic results, that benzoxazinones are highly activated due to the absence of ester-like resonance. 2-Benzoylamino-4H-3,1-benzoxazin-4-one was found to be a new, highly active chymotrypsin inactivator. In contrast, benzothiazinones were found to be resonance stabilized. The contribution of a resonance structure with an exocyclic oxanion to the overall structure of the benzothiazinones and its nonproductive binding to the active site explained their low reactivity toward chymotrypsin. (C) 1995 Academic Press, Inc.

  DOI：

  10.1006/bioo.1995.1006

文献信息

• US5652237A
  申请人：——

  公开号：US5652237A

  公开（公告）日：1997-07-29
• [EN] 2-SUBSTITUTED-4H-3,1-BENZOXAZIN-4-ONES AND BENZTHIAZIN-4-ONES AS INHIBITORS OF COMPLEMENT Clr PROTEASE FOR THE TREATMENT OF INFLAMMATORY PROCESSES<br/>[FR] 4H-3,1-BENZOXAZIN-4-ONES ET BENZTHIAZIN-4-ONES SUBSTITUES EN POSITION 2 INHIBITEURS DE LA PROTHEASE Clr DU COMPLEMENT POUR LE TRAITEMENT DES PROCESSUS INFLAMMATOIRES
  申请人：WARNER-LAMBERT COMPANY

  公开号：WO1996007648A1

  公开（公告）日：1996-03-14

  (EN) This invention concerns certain 2-substituted-3,1-benzoxazin-4-ones and benzthiazinones as complement Clr protease inhibitors and anti-inflammatory agents, pharmaceutical compositions containing them, methods of using them, and processes for their preparation.(FR) L'invention concerne certaines 3,1-benzoxazin-4-ones et benzthiazinones substituées en position 2, utilisées comme inhibiteurs de la prothéase Clr du complément et comme agents anti-inflammatoires, des compositions pharmaceutiques les renfermant, leur méthode d'utilisation et leurs procédés de préparation.
• 3,1-Benzothiazin-4-ones and 3,1-Benzoxazin-4-ones: Highly Different Activities in Chymotrypsin Inactivation
  作者：U. Neumann、M. Gutschow

  DOI：10.1006/bioo.1995.1006

  日期：1995.3

  3,1-Benzothiazin-4-ones are suIfur analogs of the potent serine protease inactivators of the 3, l-benzoxazin-4-one type, which acylate the serine residue within the active site of the enzymes. A series of 2-amino-3,1-benzothiazinones was synthesized, but these compounds showed only very little inhibitory activity toward chymotrypsin, a model serine protease. Detailed investigations revealed that benzothiazinones and benzoxazinones react with identical mechanisms, but benzothiazinones acylate chymotrypsin with much lower rate constants. Investigations of nonenzymatic hydrolysis showed the benzothiazinones to be intrinsically more stable than benzoxazinones. It was concluded from spectroscopic results, that benzoxazinones are highly activated due to the absence of ester-like resonance. 2-Benzoylamino-4H-3,1-benzoxazin-4-one was found to be a new, highly active chymotrypsin inactivator. In contrast, benzothiazinones were found to be resonance stabilized. The contribution of a resonance structure with an exocyclic oxanion to the overall structure of the benzothiazinones and its nonproductive binding to the active site explained their low reactivity toward chymotrypsin. (C) 1995 Academic Press, Inc.