6-[5-dimethylamino-1,3(2H)-dioxo-1H-isoindol-2-yl]hexyl methanesulfonate | 1599460-91-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: 6-[5-dimethylamino-1,3(2H)-dioxo-1H-isoindol-2-yl]hexyl methanesulfonate
• 英文别名: 6-(5-(dimethylamino)-1,3-dioxoisoindolin-2-yl)hexyl methanesulfonate
• CAS: 1599460-91-9
• 化学式: C₁₇H₂₄N₂O₅S
• 分子量: 368.454
• InChiKey: OWDUWMHOQOFJBA-UHFFFAOYSA-N

物化性质

• 熔点：
  79-81 °C
• 沸点：
  567.0±35.0 °C(predicted)
• 密度：
  1.279±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.89
• 重原子数：
  25.0
• 可旋转键数：
  9.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  83.99
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  6-[5-dimethylamino-1,3(2H)-dioxo-1H-isoindol-2-yl]hexyl methanesulfonate 在 盐酸 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 生成 2-(6-{1-[3-(4-cyclohexylpiperazin-1-yl)propyl]-1,2,3,4-tetrahydronaphthalen-5-yloxy}hexyl)-5-dimethylamino-1H-isoindole-1,3(2H)-dione hydrochloride
  参考文献：
  名称：

  Novel Derivatives of 1-Cyclohexyl-4-[3-(5-methoxy-1,2,3,4-tetrahydronaphthalen-1-yl)propyl]piperazine (PB28) with Improved Fluorescent and σ Receptors Binding Properties

  摘要：

  Despite the promising potentials of sigma(2) receptors in cancer therapy and diagnosis, there are still ambiguities related to the nature and physiological role of the a, protein. With the aim of providing potent and reliable tools to be used in sigma(2) receptor research, we developed a novel series of fluorescent sigma(2) ligands on the basis of our previous work, where high-affinity sigma(2) ligand 1-cyclohexyl-4-[3-(5-methoxy-1,2,3,4-tetrahydronaphthalen-1-yl)-n-propyl]piperazine (1, PB28) was used as the pharmacophore. Compared to the previous compounds, these novel ligands displayed improved fluorescence and a, binding properties, were sigma(2)-specifically taken up by breast tumor cells, and were successfully employed in confocal microscopy. Compound 14, which was the best compromise between pharmacological and fluorescent properties, was successfully employed in flow cytometry, demonstrating its potential to be used as a tool in nonradioactive binding assays for studying the affinity of putative sigma(2) receptor ligands.

  DOI：

  10.1021/jm401874n
• 作为产物：
  描述：

  6-氨基-1-己醇 在 三乙胺 、 N,N'-羰基二咪唑 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 14.0h， 生成 6-[5-dimethylamino-1,3(2H)-dioxo-1H-isoindol-2-yl]hexyl methanesulfonate
  参考文献：
  名称：

  Novel Derivatives of 1-Cyclohexyl-4-[3-(5-methoxy-1,2,3,4-tetrahydronaphthalen-1-yl)propyl]piperazine (PB28) with Improved Fluorescent and σ Receptors Binding Properties

  摘要：

  Despite the promising potentials of sigma(2) receptors in cancer therapy and diagnosis, there are still ambiguities related to the nature and physiological role of the a, protein. With the aim of providing potent and reliable tools to be used in sigma(2) receptor research, we developed a novel series of fluorescent sigma(2) ligands on the basis of our previous work, where high-affinity sigma(2) ligand 1-cyclohexyl-4-[3-(5-methoxy-1,2,3,4-tetrahydronaphthalen-1-yl)-n-propyl]piperazine (1, PB28) was used as the pharmacophore. Compared to the previous compounds, these novel ligands displayed improved fluorescence and a, binding properties, were sigma(2)-specifically taken up by breast tumor cells, and were successfully employed in confocal microscopy. Compound 14, which was the best compromise between pharmacological and fluorescent properties, was successfully employed in flow cytometry, demonstrating its potential to be used as a tool in nonradioactive binding assays for studying the affinity of putative sigma(2) receptor ligands.

  DOI：

  10.1021/jm401874n

文献信息

• Novel and Selective Fluorescent σ₂-Receptor Ligand with a 3,4-Dihydroisoquinolin-1-one Scaffold: A Tool to Study σ₂Receptors in Living Cells
  作者：Mauro Niso、Chiara Riganti、Maria Laura Pati、Dario Ghigo、Francesco Berardi、Carmen Abate

  DOI：10.1002/cbic.201402712

  日期：2015.5.4

  Lighting up the competition: A fluorescent ligand that is selective for the sigma‐2 receptor was developed and validated as an alternative to non‐selective sigma receptor probes. The novel probe was found to be competitive with prior non‐fluorescent probes and could serve as a powerful new tool for σ2 receptor research.

  点燃竞争：开发了一种对sigma-2受体具有选择性的荧光配体，并经过验证，可以替代非选择性sigma受体探针。新探发现与以前的非荧光探针竞争力，并可以作为一个σ强大的新工具2受体的研究。
• Development of sigma-1 (σ 1 ) receptor fluorescent ligands as versatile tools to study σ 1 receptors
  作者：Carmen Abate、Chiara Riganti、Maria Laura Pati、Dario Ghigo、Francesco Berardi、Timur Mavlyutov、Lian-Wang Guo、Arnold Ruoho

  DOI：10.1016/j.ejmech.2015.12.014

  日期：2016.1

  Despite their controversial physiology, sigma-1 (sigma(1)) receptors are intriguing targets for the development of therapeutic agents for central nervous system diseases. With the aim of providing versatile pharmacological tools to study sigma(1) receptors, we developed three sigma(1) fluorescent tracers by functionalizing three well characterized sigma(1) ligands with a fluorescent tag. A good compromise between sigma(1) binding affinity and fluorescent properties was reached, and the sigma(1) specific targeting of the novel tracers was demonstrated by confocal microscopy and flow cytometry. These novel ligands were also successfully used in competition binding studies by flow cytometry, showing their utility in nonradioactive binding assays as an alternative strategy to the more classical radioligand binding assays. To the best of our knowledge these are the first sigma(1) fluorescent ligands to be developed and successfully employed in living cells, representing promising tools to strengthen ai receptors related studies. (C) 2015 Elsevier Masson SAS. All rights reserved.