1-((1R,5S)-6,6-dimethylbicyclo[3.1.1]hept-2-en-2-yl)-N-((3'-fluorobiphenyl-4-yl)methyl)-N-methylmethanaminium iodide | 1313884-38-6

• 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: 1-((1R,5S)-6,6-dimethylbicyclo[3.1.1]hept-2-en-2-yl)-N-((3'-fluorobiphenyl-4-yl)methyl)-N-methylmethanaminium iodide
• 英文别名: [(1R,5S)-6,6-dimethyl-2-bicyclo[3.1.1]hept-2-enyl]methyl-[[4-(3-fluorophenyl)phenyl]methyl]-dimethylazanium;iodide
• CAS: 1313884-38-6
• 化学式: C₂₅H₃₁FN*I
• 分子量: 491.431
• InChiKey: FJOYRFNTXRAEQF-XYOGLKKJSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  3.07
• 重原子数：
  28
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  N-(4-bromobenzyl)-1-((1R,5S)-6,6-dimethylbicyclo[3.1.1]hept-2-en-2-yl)methanamine 在 四(三苯基膦)钯 、 甲酸 、 sodium carbonate 作用下， 以 二氯甲烷 、 水 、 异丙醇 、 甲苯 为溶剂， 反应 1.5h， 生成 1-((1R,5S)-6,6-dimethylbicyclo[3.1.1]hept-2-en-2-yl)-N-((3'-fluorobiphenyl-4-yl)methyl)-N-methylmethanaminium iodide
  参考文献：
  名称：

  CXCR3 antagonists: Quaternary ammonium salts equipped with biphenyl- and polycycloaliphatic-anchors

  摘要：

  Small-molecule ligands for the CXCR3 chemokine receptor receive considerable attention as a means to interrogate the roles of CXCR3 in vitro and in vivo and/or to potentially treat various conditions such as inflammatory diseases and cancer. We have synthesized and explored a novel class of small-molecule antagonists for CXCR3. A medium-throughput screen revealed an adamantane-guanidine as a hit. The guanidine unit was replaced by a small quaternary ammonium group, leading to ca. 5-fold increase in affinity. Substitution of the adamantane group by a myrtenyl moiety further increased affinity, while the benzyl group was decorated with an additional (substituted) aryl ring. This led to the identification of several bisaryl-based ligands with CXCR3 affinities of around 100 nM and with the ability to antagonize the functional activity of CXCL10. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.04.035

文献信息

• CXCR3 antagonists: Quaternary ammonium salts equipped with biphenyl- and polycycloaliphatic-anchors
  作者：Maikel Wijtmans、Dennis Verzijl、Serge Bergmans、Michael Lai、Leontien Bosch、Martine J. Smit、Iwan J.P. de Esch、Rob Leurs

  DOI：10.1016/j.bmc.2011.04.035

  日期：2011.6

  Small-molecule ligands for the CXCR3 chemokine receptor receive considerable attention as a means to interrogate the roles of CXCR3 in vitro and in vivo and/or to potentially treat various conditions such as inflammatory diseases and cancer. We have synthesized and explored a novel class of small-molecule antagonists for CXCR3. A medium-throughput screen revealed an adamantane-guanidine as a hit. The guanidine unit was replaced by a small quaternary ammonium group, leading to ca. 5-fold increase in affinity. Substitution of the adamantane group by a myrtenyl moiety further increased affinity, while the benzyl group was decorated with an additional (substituted) aryl ring. This led to the identification of several bisaryl-based ligands with CXCR3 affinities of around 100 nM and with the ability to antagonize the functional activity of CXCL10. (C) 2011 Elsevier Ltd. All rights reserved.