benzyl (S)-2-((4-((3,4-dichlorophenyl)carbamoyl)piperazin-1-yl)methyl)-4-isopropylpiperazine-1-carboxylate | 1381950-06-6

• 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: benzyl (S)-2-((4-((3,4-dichlorophenyl)carbamoyl)piperazin-1-yl)methyl)-4-isopropylpiperazine-1-carboxylate
• CAS: 1381950-06-6
• 化学式: C₂₇H₃₅Cl₂N₅O₃
• 分子量: 548.513
• InChiKey: VITFQWNRADYKDU-QHCPKHFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.87
• 重原子数：
  37.0
• 可旋转键数：
  6.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  68.36
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  benzyl (S)-2-((4-((3,4-dichlorophenyl)carbamoyl)piperazin-1-yl)methyl)-4-isopropylpiperazine-1-carboxylate 在 盐酸 、 palladium 10% on activated carbon 、 氢气 、 zinc dibromide 作用下， 以 1,4-二氧六环 、 N-甲基吡咯烷酮 、 水 为溶剂， 以60%的产率得到N-(3,4-dichlorophenyl)-4-[[(2S)-4-propan-2-ylpiperazin-2-yl]methyl]piperazine-1-carboxamide
  参考文献：
  名称：

  The design and synthesis of novel, potent and orally bioavailable N-aryl piperazine-1-carboxamide CCR2 antagonists with very high hERG selectivity

  摘要：

  A novel N-aryl piperazine-1-carboxamide series of human CCR2 chemokine receptor antagonists was discovered. Early analogues were potent at CCR2 but also inhibited the hERG cardiac ion channel. Structural modifications which decreased lipophilicity and basicity resulted in the identification of a sub-series with an improved margin over hERG. The pharmacological and pharmacokinetic properties of the lead compound from this series, N-(3,4-dichlorophenyl)-4-[(2R)-4-isopropylpiperazine-2-carbonyl]piperazine-1-carboxamide, are described. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.04.118
• 作为产物：
  描述：

  3,4-二氯苯异氰酸酯 在 三乙酰氧基硼氢化钠 、 potassium carbonate 、 三氟乙酸 作用下， 以 二氯甲烷 、 氯仿 、 丙酮 为溶剂， 生成 benzyl (S)-2-((4-((3,4-dichlorophenyl)carbamoyl)piperazin-1-yl)methyl)-4-isopropylpiperazine-1-carboxylate
  参考文献：
  名称：

  The design and synthesis of novel, potent and orally bioavailable N-aryl piperazine-1-carboxamide CCR2 antagonists with very high hERG selectivity

  摘要：

  A novel N-aryl piperazine-1-carboxamide series of human CCR2 chemokine receptor antagonists was discovered. Early analogues were potent at CCR2 but also inhibited the hERG cardiac ion channel. Structural modifications which decreased lipophilicity and basicity resulted in the identification of a sub-series with an improved margin over hERG. The pharmacological and pharmacokinetic properties of the lead compound from this series, N-(3,4-dichlorophenyl)-4-[(2R)-4-isopropylpiperazine-2-carbonyl]piperazine-1-carboxamide, are described. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.04.118