N-(4-bromobenzyl)-1-((1R,5S)-6,6-dimethylbicyclo[3.1.1]hept-2-en-2-yl)methanamine | 1313885-03-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: N-(4-bromobenzyl)-1-((1R,5S)-6,6-dimethylbicyclo[3.1.1]hept-2-en-2-yl)methanamine
• CAS: 1313885-03-8
• 化学式: C₁₇H₂₂BrN
• 分子量: 320.272
• InChiKey: FTXGCYYQVIOFLS-HOCLYGCPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.53
• 重原子数：
  19.0
• 可旋转键数：
  4.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  12.03
• 氢给体数：
  1.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  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 水 、 异丙醇 、 甲苯 为溶剂， 反应 1.5h， 生成 1-(4'-chlorobiphenyl-4-yl)-N-(((1R,5S)-6,6-dimethylbicyclo[3.1.1]hept-2-en-2-yl)methyl)-N-methylmethanamine
  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
• 作为产物：
  描述：

  桃金娘烯醛 、 4-溴苄胺盐酸盐 在 三乙酰氧基硼氢化钠 、 三乙胺 、 sodium hydroxide 作用下， 以 1,2-二氯乙烷 、 水 为溶剂， 反应 48.17h， 以22%的产率得到N-(4-bromobenzyl)-1-((1R,5S)-6,6-dimethylbicyclo[3.1.1]hept-2-en-2-yl)methanamine
  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