2-(2-Iodo-phenylamino)-naphtho[2,3-d][1,3]oxazin-4-one

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-(2-Iodo-phenylamino)-naphtho[2,3-d][1,3]oxazin-4-one
• 英文别名: 2-(2-iodoanilino)benzo[g][3,1]benzoxazin-4-one
• 化学式: C₁₈H₁₁IN₂O₂
• 分子量: 414.202
• InChiKey: AEMRKAJMXFCCAC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  50.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-iodoaniline hydrochloride 在 硫酸 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 38.0h， 生成 2-(2-Iodo-phenylamino)-naphtho[2,3-d][1,3]oxazin-4-one
  参考文献：
  名称：

  2-Amino-4H-3,1-benzoxazin-4-ones as Inhibitors of C1r Serine Protease

  摘要：

  A series of 2-amino-4H-3,1-benzoxazin-4-ones have been synthesized and evaluated as inhibitors of the complement enzyme C1r. C1r is a serine protease at the beginning of the complement cascade, and complement activation by beta-amyloid may represent a major contributing pathway to the neuropathology of Alzheimer's disease. Compounds such as 7-chloro-2-[(2-iodophenyl)amino]benz[d][1,3]oxazin-4-one (32) and 7-methyl-2-[(2-iodophenyl)amino]benz[d] 4-one (37) show improved potency compared to the reference compound FUT-175. Many of these active compounds also possess increased selectivity for C1r compared to trypsin and enhanced hydrolytic stability relative to 2-(2-iodophenyl)-4H-3,1-benzoxazin-4-one (1).

  DOI：

  10.1021/jm970394d

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.
• 2-Amino-4<i>H</i>-3,1-benzoxazin-4-ones as Inhibitors of C1r Serine Protease
  作者：Sheryl J. Hays、Bradley W. Caprathe、John L. Gilmore、Nilam Amin、Mark R. Emmerling、Walter Michael、Ravi Nadimpalli、Rathna Nath、Kadee J. Raser、Daniel Stafford、Desiree Watson、Kevin Wang、Juan C. Jaen

  DOI：10.1021/jm970394d

  日期：1998.3.1

  A series of 2-amino-4H-3,1-benzoxazin-4-ones have been synthesized and evaluated as inhibitors of the complement enzyme C1r. C1r is a serine protease at the beginning of the complement cascade, and complement activation by beta-amyloid may represent a major contributing pathway to the neuropathology of Alzheimer's disease. Compounds such as 7-chloro-2-[(2-iodophenyl)amino]benz[d][1,3]oxazin-4-one (32) and 7-methyl-2-[(2-iodophenyl)amino]benz[d] 4-one (37) show improved potency compared to the reference compound FUT-175. Many of these active compounds also possess increased selectivity for C1r compared to trypsin and enhanced hydrolytic stability relative to 2-(2-iodophenyl)-4H-3,1-benzoxazin-4-one (1).