N-((9H-fluoren-2-yl)methyl)-1-((1R,5S)-6,6-dimethylbicyclo[3.1.1]hept-2-en-2-yl)-N-methylmethanamine | 1313884-74-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: N-((9H-fluoren-2-yl)methyl)-1-((1R,5S)-6,6-dimethylbicyclo[3.1.1]hept-2-en-2-yl)-N-methylmethanamine
• 英文别名: 1-[(1R,5S)-6,6-dimethyl-2-bicyclo[3.1.1]hept-2-enyl]-N-(9H-fluoren-2-ylmethyl)-N-methylmethanamine
• CAS: 1313884-74-0
• 化学式: C₂₅H₂₉N
• 分子量: 343.512
• InChiKey: QVJJBJLTAASBMH-URXFXBBRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  3.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  N-((9H-fluoren-2-yl)methyl)-1-((1R,5S)-6,6-dimethylbicyclo[3.1.1]hept-2-en-2-yl)-N-methylmethanamine 、 碘甲烷 以 二氯甲烷 为溶剂， 以62%的产率得到N-((9H-fluoren-2-yl)methyl)-1-((1R,5S)-6,6-dimethylbicyclo[3.1.1]hept-2-en-2-yl)-N-methylmethanaminium chloride
  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 在 sodium tetrahydroborate 、 三乙酰氧基硼氢化钠 作用下， 以 甲醇 、 乙醇 、 1,2-二氯乙烷 为溶剂， 反应 23.17h， 生成 N-((9H-fluoren-2-yl)methyl)-1-((1R,5S)-6,6-dimethylbicyclo[3.1.1]hept-2-en-2-yl)-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

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.