1-[4-(4-[benzhydrylamino]pyrimidin-2-yl)piperazin-1-yl]ethanone | 1337976-39-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-[4-(4-[benzhydrylamino]pyrimidin-2-yl)piperazin-1-yl]ethanone
• 英文别名: 1-[4-[4-(Benzhydrylamino)pyrimidin-2-yl]piperazin-1-yl]ethanone
• CAS: 1337976-39-2
• 化学式: C₂₃H₂₅N₅O
• 分子量: 387.484
• InChiKey: CCGCMKRPCWRKHM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  29
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  61.4
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  二苯甲胺 在 N,N-二异丙基乙胺 作用下， 以 乙醇 、 正丁醇 为溶剂， 反应 4.08h， 生成 1-[4-(4-[benzhydrylamino]pyrimidin-2-yl)piperazin-1-yl]ethanone
  参考文献：
  名称：

  Development of 2-substituted-N-(naphth-1-ylmethyl) and N-benzhydrylpyrimidin-4-amines as dual cholinesterase and Aβ-aggregation inhibitors: Synthesis and biological evaluation

  摘要：

  A group of 2-substituted N-(naphth-1-ylmethyl)pyrimidin-4-amines (6a-k) and N-benzhydrylpyrimidin4-amines (7a-k) in conjunction with varying steric and electronic properties at the C-2 position were designed, synthesized and evaluated as dual cholinesterase and amyloid-beta (A beta)-aggregation inhibitors. The naphth-1-ylmethyl compound 6f (2-(4-cyclohexylpiperazin-1-yl)-N-(naphth-1-ylmethyl)pyrimidin-4-amine) exhibited optimum dual ChE (AChE IC50 = 8.0 mu M, BuChE IC50 = 3.9 mu M) and hAChE-promoted A beta-aggregation inhibition (30.8% at 100 mu M), whereas in the N-benzhydryl series, compound 7f (N-benzhydryl-2-(4-cyclohexylpiperazin-1-yl)pyrimidin-4-amine) exhibited optimum combination of dual ChE (AChE IC50 = 10.0 mu M, BuChE IC50 = 7.6 mu M) and hAChE-promoted A beta-aggregation inhibition (32% at 100 mu M). These results demonstrate that a 2,4-disubstituted pyrimidine ring serves as a suitable template to target multiple pathological routes in AD, with a C-2 cyclohexylpiperazine substituent providing dual ChE inhibition and potency whereas a C-4 diphenylmethane substituent provides A beta-aggregation inhibition. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.07.091

文献信息

• Development of 2-substituted-N-(naphth-1-ylmethyl) and N-benzhydrylpyrimidin-4-amines as dual cholinesterase and Aβ-aggregation inhibitors: Synthesis and biological evaluation
  作者：Tarek Mohamed、Jacky C.K. Yeung、Praveen P.N. Rao

  DOI：10.1016/j.bmcl.2011.07.091

  日期：2011.10

  A group of 2-substituted N-(naphth-1-ylmethyl)pyrimidin-4-amines (6a-k) and N-benzhydrylpyrimidin4-amines (7a-k) in conjunction with varying steric and electronic properties at the C-2 position were designed, synthesized and evaluated as dual cholinesterase and amyloid-beta (A beta)-aggregation inhibitors. The naphth-1-ylmethyl compound 6f (2-(4-cyclohexylpiperazin-1-yl)-N-(naphth-1-ylmethyl)pyrimidin-4-amine) exhibited optimum dual ChE (AChE IC50 = 8.0 mu M, BuChE IC50 = 3.9 mu M) and hAChE-promoted A beta-aggregation inhibition (30.8% at 100 mu M), whereas in the N-benzhydryl series, compound 7f (N-benzhydryl-2-(4-cyclohexylpiperazin-1-yl)pyrimidin-4-amine) exhibited optimum combination of dual ChE (AChE IC50 = 10.0 mu M, BuChE IC50 = 7.6 mu M) and hAChE-promoted A beta-aggregation inhibition (32% at 100 mu M). These results demonstrate that a 2,4-disubstituted pyrimidine ring serves as a suitable template to target multiple pathological routes in AD, with a C-2 cyclohexylpiperazine substituent providing dual ChE inhibition and potency whereas a C-4 diphenylmethane substituent provides A beta-aggregation inhibition. (C) 2011 Elsevier Ltd. All rights reserved.