1-(2-bromo-benzyl)-4-phenyl-piperazine | 198707-65-2

• 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-phenyl-piperazine
• 英文别名: Piperazine, 1-[(2-bromophenyl)methyl]-4-phenyl-；1-[(2-bromophenyl)methyl]-4-phenylpiperazine
• CAS: 198707-65-2
• 化学式: C₁₇H₁₉BrN₂
• 分子量: 331.255
• InChiKey: QDSUWCFUDBSVMO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  20
• 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：

  N-苯基哌嗪 、 邻溴苯甲醛 在 sodium cyanoborohydride 作用下， 以 甲醇 为溶剂， 反应 6.0h， 以42%的产率得到1-(2-bromo-benzyl)-4-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

• Modulators of molecules with phosphotyrosine recognition units
  申请人：Novo Nordisk A/S

  公开号：US06043247A1

  公开（公告）日：2000-03-28

  The present invention relates to novel substituted acrylic acids, to methods for their preparation, compositions containing them, and their use for treatment of human and animal disorders, to their use for purification of proteins or glycoproteins, and to their use in diagnosis. The invention also relates to modulation of the activity of molecules with phospho-tyrosine recognition units, including protein tyrosine phosphatases (PTPases) and proteins with Src-homology-2 domains, in in vitro systems, microorganisms, eukaryotic cells, whole animals and human beings.

  本发明涉及新型取代丙烯酸，其制备方法，含有它们的组合物，以及它们用于治疗人类和动物疾病的用途，用于蛋白质或糖蛋白的纯化，以及在诊断中的应用。该发明还涉及通过磷酸酪氨酸识别单元调节分子活性，包括蛋白酪氨酸磷酸酶（PTPases）和具有Src同源2结构域的蛋白质，在体外系统、微生物、真核细胞、整个动物和人类中的应用。
• US6043247A
  申请人：——

  公开号：US6043247A

  公开（公告）日：2000-03-28
• [EN] MODULATORS OF MOLECULES WITH PHOSPHOTYROSINE RECOGNITION UNITS<br/>[FR] MODULATEURS DE MOLECULES POSSEDANT DES UNITES DE RECONNAISSANCE DE LA PHOSPHOTYROSINE
  申请人：NOVO NORDISK A/S

  公开号：WO1997039748A1

  公开（公告）日：1997-10-30

  (EN) The present invention relates to novel organic compounds, to methods for their preparation, to compositions containing them, to their use for treatment of human and animal disorders, to their use for purification of proteins or glycoproteins, and to their use in diagnosis. The invention relates to modulation of the activity of molecules with phospho-tyrosine recognition units, including protein tyrosine phosphatases (PTPases) and proteins with Src-homology-2 domains, in $i(in vitro) systems, micro-organisms, eukaryotic cells, whole animals and human beings. The novel organic compounds are compounds of general formula (I) wherein (L)n, n, Ar1 and R1 are defined as defined in the application.(FR) Cette invention concerne de nouveaux composés organiques, des procédés de préparation de ces composés et des compositions les contenant: cette invention concerne également l'utilisation de ces composés dans le traitement de troubles chez l'homme et chez les animaux, dans la purification de protéines ou de glycoprotéines, et dans des diagnostics. Cette invention concerne en outre la modulation, dans des systèmes $i(in vitro), de l'activité de molécules possédant des unités de reconnaissance de la phosphotyrosine, y compris des protéines tyrosine phosphatases (PTPases) et des protéines possédant des domaines Src-homologie-2. Cette invention concerne enfin des micro-organismes, des cellules eucaryotes, ainsi que des animaux et des êtres humains dans leur ensemble. Ces nouveaux composés organiques correspondent à la formule générale (I) où (L)n, n, Ar1 et R1 sont tels que définis dans la description.
• Arylpiperazines displaying preferential potency against chloroquine-resistant strains of the malaria parasite Plasmodium falciparum
  作者：Carrie-Anne Molyneaux、Miriam Krugliak、Hagai Ginsburg、Kelly Chibale

  DOI：10.1016/j.bcp.2005.10.023

  日期：2005.12

  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.