(2,6-Dichloro-phenyl)-6-methyl-4H-3,1-benzoxazin-4-one

• 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: (2,6-Dichloro-phenyl)-6-methyl-4H-3,1-benzoxazin-4-one
• 英文别名: 2-(2,6-Dichloro-phenyl)-6-methyl-4H-3,1-benzoxazin-4-one；2-(2,6-dichlorophenyl)-6-methyl-3,1-benzoxazin-4-one
• 化学式: C₁₅H₉Cl₂NO₂
• 分子量: 306.148
• InChiKey: FKSQQMFGMVENBR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  38.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-氨基-5-甲基苯甲酸 、 2,6-二氯苯甲酰氯 在 三乙胺 作用下， 以 甲苯 为溶剂， 反应 25.0h， 以11%的产率得到(2,6-Dichloro-phenyl)-6-methyl-4H-3,1-benzoxazin-4-one
  参考文献：
  名称：

  Inhibitors of the tissue factor/factor VIIa-induced coagulation: synthesis and in vitro evaluation of novel specific 2-aryl substituted 4 H -3,1-benzoxazin-4-ones

  摘要：

  The synthesis of a series of novel 2-aryl substituted 4H-3,1-benzoxazin-4-ones and their evaluation as specific inhibitors of the Tissue Factor (TF)/Factor VIIa (FVIIa)-induced pathway of coagulation is reported. Inhibitory activities (IC50 values) in the range 0.17 to > 40 mu M on the activation of Factor X (FX) by the TF/FVIIa complex were found for compounds having one or two electronegative substituents such as F, Cl and NO2 in the 2-aryl substituent. Different substitutions both electron-attracting and donating groups were allowed in the 5, 6, 7 and 8 positions. Several of the compounds showed a selectivity ratio towards FX and thrombin of > 50, thus being the first small molecules described as potential drugs for oral antithrombotic treatment without side effects such as bleeding which is observed especially with thrombin inhibitors. The best substituent pattern being the 2-aryl group substituted with: 2-F; 2,6-F-2; or 2-FX; 6-Cl; together with electronegative substitution in the 5, 6, 7, or 8 positions. 7-Heteroaryl substituents like thienyl and furanyl were of low activity while some 2-(2-chloro-3-pyridyl) derivatives had inhibitory activity < 10 mu M and a good selectivity. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(00)00129-2

文献信息

• US6180625
  申请人：——

  公开号：——

  公开（公告）日：——
• US06180625B2
  申请人：——

  公开号：——

  公开（公告）日：——
• USE OF FUSED HETEROCYCLIC COMPOUNDS AS SCCE INHIBITORS FOR THE TREATMENT OF SKIN CONDITIONS OR CANCER
  申请人：Arexis AB

  公开号：EP1631295A2

  公开（公告）日：2006-03-08
• Use of heterocyclic compounds as scce inhibitors
  申请人：Linschoten Marcel

  公开号：US20060258651A1

  公开（公告）日：2006-11-16

  The present invention relates to heterocyclic inhibitors of stratum corneum chymotryptic enzyme (SCCE). More particularly, the invention relates to the use of compounds with the formula (I) or (II) for treatment of certain diseases, in particular skin diseases such as pruirtus, as well as cancer such as ovarian cancer.
• US6180625B1
  申请人：——

  公开号：US6180625B1

  公开（公告）日：2001-01-30