2-(3-bromophenyl)-2-methyl-2,3-dihydro-4H-1,3-benzoxazin-4-one | 937371-38-5

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: 2-(3-bromophenyl)-2-methyl-2,3-dihydro-4H-1,3-benzoxazin-4-one
• 英文别名: 2-(3-bromophenyl)-2-methyl-3H-1,3-benzoxazin-4-one
• CAS: 937371-38-5
• 化学式: C₁₅H₁₂BrNO₂
• 分子量: 318.17
• InChiKey: CBDCPWBARIEQJW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(3-bromophenyl)-2-methyl-2,3-dihydro-4H-1,3-benzoxazin-4-one 在 五氯化磷 、 N,N-二异丙基乙胺 、 三氯氧磷 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 19.0h， 生成 2-(3-bromophenyl)-N-methoxy-2-methyl-1,3-benzoxazin-4-amine
  参考文献：
  名称：

  Core Refinement toward Permeable β-Secretase (BACE-1) Inhibitors with Low hERG Activity

  摘要：

  By use of iterative design aided by predictive models for target affinity, brain permeability, and hERG activity, novel and diverse compounds based on cyclic amidine and guanidine cores were synthesized with the goal of finding BACE-1 inhibitors as a treatment for Alzheimer's disease. Since synthesis feasibility had low priority in the design of the cores, an extensive synthesis effort was needed to make the relevant compounds. Syntheses of these compounds are reported, together with physicochemical properties and structure-activity relationships based on in vitro data. Four crystal structures of diverse amidines binding in the active site are deposited and discussed. Inhibitors of BACE-1 with 3 mu M to 32 nM potencies in cells are shown, together with data on in vivo brain exposure levels for four compounds. The results presented show the importance of the core structure for the profile of the final compounds.

  DOI：

  10.1021/jm3011349
• 作为产物：
  描述：

  3'-溴苯乙酮 、 水杨酰胺 在 对甲苯磺酸 作用下， 以 甲苯 为溶剂， 以81%的产率得到2-(3-bromophenyl)-2-methyl-2,3-dihydro-4H-1,3-benzoxazin-4-one
  参考文献：
  名称：

  WO2007/58583

  摘要：

  公开号：

文献信息

• Novel 2-Amino-Heterocycles Useful in the Treatment of Abeta-Related Pathologies
  申请人：Albert Jeffrey

  公开号：US20080293709A1

  公开（公告）日：2008-11-27

  This invention relates to novel compounds having the structural formula I below: and to their pharmaceutically acceptable salts, compositions and methods of use. These novel compounds provide a treatment or prophylaxis of cognitive impairment, Alzheimer Disease, neurodegeneration and dementia.

  本发明涉及具有下面结构式I的新化合物，以及它们的药学上可接受的盐、组合物和使用方法。这些新化合物提供了治疗或预防认知障碍、阿尔茨海默病、神经退行性疾病和痴呆症的方法。
• NOVEL 2-AMINO-HETEROCYCLES UDEFUL IN THE TREATMENT OF ABETA-RELATED PATHOLOGIES
  申请人：Astra Zeneca AB

  公开号：EP1957462A2

  公开（公告）日：2008-08-20
• [EN] COMPOUNDS AND USES THEREOF IV<br/>[FR] COMPOSES ET LEURS UTILISATIONS
  申请人：ASTRAZENECA AB

  公开号：WO2007058583A2

  公开（公告）日：2007-05-24

  [EN] This invention relates to novel compounds having the structural formula I below: and to their pharmaceutically acceptable salts, compositions and methods of use. These novel compounds provide a treatment or prophylaxis of cognitive impairment, Alzheimer Disease, neurodegeneration and dementia.
  [FR] L'invention concerne des nouveaux composés de formule structurelle (I) et leurs sels pharmaceutiquement acceptables, leurs compositions et leurs procédés d'utilisation. Les nouveaux composés de l'invention sont utilisés dans le traitement ou la prophylaxie d'une déficience cognitive, de la maladie d'Alzheimer, de la neurodégénérescence et de la démence.