(1S)-bornane-carbaldehyde-(2ξ) | 1159913-47-9

• 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: (1S)-bornane-carbaldehyde-(2ξ)
• 英文别名: (1S)-Bornan-carbaldehyd-(2ξ)；(1S,4R)-1,7,7-trimethylbicyclo[2.2.1]heptane-2-carbaldehyde
• CAS: 1159913-47-9
• 化学式: C₁₁H₁₈O
• 分子量: 166.263
• InChiKey: XKOGXRMDXIYVDT-RTVRGBPTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (1S)-bornane-carbaldehyde-(2ξ) 在 甲酸 、 三乙酰氧基硼氢化钠 、 三乙胺 作用下， 以 水 、 1,2-二氯乙烷 为溶剂， 反应 0.17h， 生成 endo/exo-N-(4-iodobenzyl)-N-mehyl-1-((1S,4R)-1,7,7-trimethylbicyclo[2.2.1]heptan-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
• 作为产物：
  描述：

  (1R,4R)-2-(methoxymethylene)-1,7,7-trimethylbicyclo[2.2.1]heptane 在 盐酸 、 水 作用下， 以 四氢呋喃 为溶剂， 反应 2.5h， 生成 (1S)-bornane-carbaldehyde-(2ξ)
  参考文献：
  名称：

  Exploring a pocket for polycycloaliphatic groups in the CXCR3 receptor with the aid of a modular synthetic strategy

  摘要：

  A CXCR3 pocket capable of accommodating polycycloaliphatics was explored using a modular synthetic strategy. The systematic studies reveal that the tricyclic 2-adamantane and bicyclic (iso) bornyl group are efficiently recognized by CXCR3. (c) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.02.093

文献信息

• Riviere, Annales de Chimie (Cachan, France), 1946, vol. <12> 1, p. 157,183
  作者：Riviere

  DOI：——

  日期：——
• Vavon; Riviere, Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1945, vol. 220, p. 286
  作者：Vavon、Riviere

  DOI：——

  日期：——
• 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.
• Exploring a pocket for polycycloaliphatic groups in the CXCR3 receptor with the aid of a modular synthetic strategy
  作者：Maikel Wijtmans、Dennis Verzijl、Cindy M.E. van Dam、Leontien Bosch、Martine J. Smit、Rob Leurs、Iwan J.P. de Esch

  DOI：10.1016/j.bmcl.2009.02.093

  日期：2009.4

  A CXCR3 pocket capable of accommodating polycycloaliphatics was explored using a modular synthetic strategy. The systematic studies reveal that the tricyclic 2-adamantane and bicyclic (iso) bornyl group are efficiently recognized by CXCR3. (c) 2009 Elsevier Ltd. All rights reserved.