3-(4-(3-bromophenyl)-4-oxobutanoyl)benzonitrile | 1014980-72-3

• 英文名称: 3-(4-(3-bromophenyl)-4-oxobutanoyl)benzonitrile
• CAS: 1014980-72-3
• 化学式: C₁₇H₁₂BrNO₂
• 分子量: 342.192
• InChiKey: MRLHOLNYFZEJSM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.17
• 重原子数：
  21.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  57.93
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  3-(4-(3-bromophenyl)-4-oxobutanoyl)benzonitrile 、 聚甘氨酸 在 对甲苯磺酸 作用下， 以 乙醇 为溶剂， 反应 72.0h， 生成 2-(2-(3-bromophenyl)-5-(3-cyanophenyl)-1H-pyrrol-1-yl)acetic acid
  参考文献：
  名称：

  Acylguanidine inhibitors of β-secretase: Optimization of the pyrrole ring substituents extending into the S1 and S3 substrate binding pockets

  摘要：

  Proteolytic cleavage of amyloid precursor protein by beta-secretase (BACE-1) and gamma-secretase leads to formation of beta-amyloid (A beta) a key component of amyloid plaques, which are considered the hallmark of Alzheimer's disease. Small molecule inhibitors of BACE-1 may reduce levels of A beta and thus have therapeutic potential for treating Alzheimer's disease. We recently reported the identification of a novel small molecule BACE-1 inhibitor N-[2-(2,5-diphenyl-pyrrol-1-yl)-acetyl]guanidine (3.a.1). We report here the initial hit-to-lead optimization of this hit and the SAR around the aryl groups occupying the S-1 and S-2' pockets leading to submicromolar BACE-1 inhibitors. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.12.010
• 作为产物：
  描述：

  3-乙酰苯腈 、 2,3-二溴苯乙酮 在 二乙胺 、 zinc(II) chloride 、 叔丁醇 作用下， 以 甲苯 为溶剂， 生成 3-(4-(3-bromophenyl)-4-oxobutanoyl)benzonitrile
  参考文献：
  名称：

  Acylguanidine inhibitors of β-secretase: Optimization of the pyrrole ring substituents extending into the S1 and S3 substrate binding pockets

  摘要：

  Proteolytic cleavage of amyloid precursor protein by beta-secretase (BACE-1) and gamma-secretase leads to formation of beta-amyloid (A beta) a key component of amyloid plaques, which are considered the hallmark of Alzheimer's disease. Small molecule inhibitors of BACE-1 may reduce levels of A beta and thus have therapeutic potential for treating Alzheimer's disease. We recently reported the identification of a novel small molecule BACE-1 inhibitor N-[2-(2,5-diphenyl-pyrrol-1-yl)-acetyl]guanidine (3.a.1). We report here the initial hit-to-lead optimization of this hit and the SAR around the aryl groups occupying the S-1 and S-2' pockets leading to submicromolar BACE-1 inhibitors. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.12.010