6-amino-2-(6-{1-[3-(4-cyclohexylpiperazin-1-yl)propyl]-1,2,3,4-tetrahydronaphthalen-5-yloxy}hexyl)-1H-benzo[de]isoquinoline-1,3(2H)-dione | 1599460-89-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异喹啉及其衍生物
• 英文名称: 6-amino-2-(6-{1-[3-(4-cyclohexylpiperazin-1-yl)propyl]-1,2,3,4-tetrahydronaphthalen-5-yloxy}hexyl)-1H-benzo[de]isoquinoline-1,3(2H)-dione
• 英文别名: 6-Amino-2-[6-[[5-[3-(4-cyclohexylpiperazin-1-yl)propyl]-5,6,7,8-tetrahydronaphthalen-1-yl]oxy]hexyl]benzo[de]isoquinoline-1,3-dione；6-amino-2-[6-[[5-[3-(4-cyclohexylpiperazin-1-yl)propyl]-5,6,7,8-tetrahydronaphthalen-1-yl]oxy]hexyl]benzo[de]isoquinoline-1,3-dione
• CAS: 1599460-89-5
• 化学式: C₄₁H₅₄N₄O₃
• 分子量: 650.905
• InChiKey: FXSQHPHHAIFUIN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.1
• 重原子数：
  48
• 可旋转键数：
  13
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  79.1
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  6-amino-2-(6-{1-[3-(4-cyclohexylpiperazin-1-yl)propyl]-1,2,3,4-tetrahydronaphthalen-5-yloxy}hexyl)-1H-benzo[de]isoquinoline-1,3(2H)-dione 在 盐酸 作用下， 生成 6-amino-2-(6-{1-[3-(4-cyclohexylpiperazin-1-yl)propyl]-1,2,3,4-tetrahydronaphthalen-5-yloxy}hexyl)-1H-benzo[de]isoquinoline-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-[1-[3-(4-cyclohexylpiperazin-1-yl)propyl]-1,2,3,4-tetrahydronaphthalen-5-yloxy]hexylamine 在 palladium 10% on activated carbon 、 氢气 作用下， 以 乙醇 为溶剂， 反应 15.0h， 生成 6-amino-2-(6-{1-[3-(4-cyclohexylpiperazin-1-yl)propyl]-1,2,3,4-tetrahydronaphthalen-5-yloxy}hexyl)-1H-benzo[de]isoquinoline-1,3(2H)-dione
  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 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
  作者：Carmen Abate、Mauro Niso、Roberta Marottoli、Chiara Riganti、Dario Ghigo、Savina Ferorelli、Giulia Ossato、Roberto Perrone、Enza Lacivita、Don C. Lamb、Francesco Berardi

  DOI：10.1021/jm401874n

  日期：2014.4.24

  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.