1-(2-Bromo-benzyl)-4-(2-chloro-phenyl)-piperazine

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 英文名称: 1-(2-Bromo-benzyl)-4-(2-chloro-phenyl)-piperazine
• 英文别名: 1-[(2-Bromophenyl)methyl]-4-(2-chlorophenyl)piperazine
• 化学式: C₁₇H₁₈BrClN₂
• 分子量: 365.7
• InChiKey: TYHZZRPIPVTCAE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  6.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  1-(邻氯苯基)哌嗪盐酸盐 在 macroporous triethylammonium methylpolystyrene carbonate 、 sodium cyanoborohydride 作用下， 以 甲醇 为溶剂， 反应 6.0h， 生成 1-(2-Bromo-benzyl)-4-(2-chloro-phenyl)-piperazine
  参考文献：
  名称：

  Arylpiperazines displaying preferential potency against chloroquine-resistant strains of the malaria parasite Plasmodium falciparum

  摘要：

  Arylpiperazines in which the terminal secondary amino group is unsubstituted were found to display a mefloquine-type antimalarial behavior in being significantly more potent against the chloroquine-resistant (W2 and FCR3) strains of Plasmodium falciparum than against the chloroquine-sensitive (D10 and NF54) strains. Substitution of the aforementioned amino group led to a dramatic drop in activity across all strains as well as abolition of the preferential potency against resistant strains that was observed for the unsubstituted counterparts. The data suggest that unsubstituted arylpiperazines are not well-recognized by the chloroquine resistance mechanism and may imply that they act mechanistically differently from chloroquine. On the other hand, 4-aminoquinoline-based heteroarylpiperazines in which the terminal secondary amino group is also unsubstituted, were found to be equally active against the chloroquine -resistant and chloroquine-sensitive strains, suggesting that chloroquine cross-resistance is not observed with these two 4-aminoquinolines. In contrast, two 4-aminoquinoline-based heteroarylpiperazines are positively recognized by the chloroquine resistance mechanism. These studies provide structural features that determine the antimalarial activity of arylpiperazines for further development, particularly against chloroquine-resistant strains. (c) 2005 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.bcp.2005.10.023

文献信息

• Discovery of a dopamine D4 selective PET ligand candidate taking advantage of a click chemistry based REM linker
  作者：Rainer Tietze、Stefan Löber、Harald Hübner、Peter Gmeiner、Torsten Kuwert、Olaf Prante

  DOI：10.1016/j.bmcl.2007.12.026

  日期：2008.2

  Employing D4 selective azaindoles as lead compounds, a focused library of the carbocyclic arene bioisosteres 1 was synthesized when we took advantage of the click chemistry derived triazolylmethyl acrylate resin 2. Ligand binding assays on monoaminergic GPCRs led to SARs that indicated further lead structure optimizations when the attachment of alkoxy substituents provided both an improvement of the biological properties and the opportunity to introduce F-18 as a radioisotope. Finally, radiosynthesis resulted in formation of the radioligand [F-18]7h that showed optimal logD(7.4) of 2.8 and was determined to be highly stable in human serum. Thus, [F-18]7h represents a promising dopamine D4 selective radioligand for positron emission tomography (PET). (C) 2007 Elsevier Ltd. All rights reserved.