(R,S)-2-(4-benzhydrylpiperazin-1-yl)-N-(4-chlorobenzyl)-4-hydroxybutanamide | 1265227-38-0

• 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: (R,S)-2-(4-benzhydrylpiperazin-1-yl)-N-(4-chlorobenzyl)-4-hydroxybutanamide
• 英文别名: 2-(4-benzhydrylpiperazin-1-yl)-N-(4-chlorobenzyl)-4-hydroxybutanamide；2-(4-benzhydrylpiperazin-1-yl)-N-[(4-chlorophenyl)methyl]-4-hydroxybutanamide
• CAS: 1265227-38-0
• 化学式: C₂₈H₃₂ClN₃O₂
• 分子量: 478.034
• InChiKey: NYWSABPTDMTDJF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  34
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  55.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  (R,S)-3-(4-benzhydrylpiperazin-1-yl)dihydrofuran-2(3H)-one 、 对氯苄胺 以 甲苯 为溶剂， 反应 12.0h， 以20%的产率得到(R,S)-2-(4-benzhydrylpiperazin-1-yl)-N-(4-chlorobenzyl)-4-hydroxybutanamide
  参考文献：
  名称：

  Synthesis and biological evaluation of new derivatives of 2-substituted 4-hydroxybutanamides as GABA uptake inhibitors

  摘要：

  This study presents the synthesis of novel substituted 4-hydroxybutanamides and their influence on the activity of murine GABA transport proteins GAT1-GAT4. The active compounds, derivatives of N-aryl-alkyl-2-(4-diphenylmethylpiperazin-1-yl)-4-hydroxybutyramide, are characterized by pIC(50) values in range of 3.92-5.06 and by slight subtype-selectivity. Among them N-4-chlorobenzylamide was the most potent GAT inhibitor (mGAT3), while N-benzylamide was the most active in GAT1-binding assay (pK(i) = 4.96). The results pointed out that benzhydryl and benzylamide moieties are crucial for the activity of this class of compounds as murine GAT inhibitors. (C) 2010 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2010.11.001

文献信息

• Synthesis and biological evaluation of new derivatives of 2-substituted 4-hydroxybutanamides as GABA uptake inhibitors
  作者：Katarzyna Kulig、Krzysztof Więckowski、Anna Więckowska、Justyna Gajda、Bartłomiej Pochwat、Georg C. Höfner、Klaus T. Wanner、Barbara Malawska

  DOI：10.1016/j.ejmech.2010.11.001

  日期：2011.1

  This study presents the synthesis of novel substituted 4-hydroxybutanamides and their influence on the activity of murine GABA transport proteins GAT1-GAT4. The active compounds, derivatives of N-aryl-alkyl-2-(4-diphenylmethylpiperazin-1-yl)-4-hydroxybutyramide, are characterized by pIC(50) values in range of 3.92-5.06 and by slight subtype-selectivity. Among them N-4-chlorobenzylamide was the most potent GAT inhibitor (mGAT3), while N-benzylamide was the most active in GAT1-binding assay (pK(i) = 4.96). The results pointed out that benzhydryl and benzylamide moieties are crucial for the activity of this class of compounds as murine GAT inhibitors. (C) 2010 Elsevier Masson SAS. All rights reserved.