2-[5-[4-(2-methoxyphenyl)-1-piperazinyl]pentyl]-6-nitro-1H-benz[de]isoquinoline-1,3(2H)-dione | 1187431-76-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-[5-[4-(2-methoxyphenyl)-1-piperazinyl]pentyl]-6-nitro-1H-benz[de]isoquinoline-1,3(2H)-dione
• 英文别名: 2-[5-[4-(2-Methoxyphenyl)piperazin-1-yl]pentyl]-6-nitrobenzo[de]isoquinoline-1,3-dione
• CAS: 1187431-76-0
• 化学式: C₂₈H₃₀N₄O₅
• 分子量: 502.57
• InChiKey: VYRJLIIWNFRNLK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  37
• 可旋转键数：
  8
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  98.9
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2-[5-[4-(2-methoxyphenyl)-1-piperazinyl]pentyl]-6-nitro-1H-benz[de]isoquinoline-1,3(2H)-dione 在 palladium 10% on activated carbon 、 一水合肼 作用下， 以 乙醇 为溶剂， 以40%的产率得到6-amino-2-[5-[4-(2-methoxyphenyl)-1-piperazinyl]pentyl]-1H-benz[de]isoquinoline-1,3(2H)-dione
  参考文献：
  名称：

  Synthesis and Characterization of Environment-Sensitive Fluorescent Ligands for Human 5-HT_1A Receptors with 1-Arylpiperazine Structure

  摘要：

  A series of "long-chain" 1-(2-methoxyphenyl)piperzine derivatives containing an environment-sensitive fluorescent moiety (4-amino-1,8-naphthalimide, 4-dimethylaminophthalimide, dansyl) was synthesized. The compounds displayed very high to moderate 5-HT1A receptor affinity and good fluorescence properties. 6-Amino-2-[5-[4-(2-methoxyphenyl)-1-piperazinyl]pentyl]-1H-benz[de]isoquinoline-1,3(2H)-dione (4) combined very high 5-HT1A receptor affinity (K-i = 0.67 nM), high fluorescence emission in CHCl3, and undetectable fluorescence emission in aqueous solution. It was evaluated for its ability to visualize 5-HT1A receptors overexpressed in CHO cells by fluorescence microscopy.

  DOI：

  10.1021/jm900706d
• 作为产物：
  描述：

  4-硝基-1,8-萘醛酸酐 、 5-(4-(2-methoxyphenyl)piperazin-1-yl)pentan-1-amine 以 乙醇 为溶剂， 反应 3.0h， 以40%的产率得到2-[5-[4-(2-methoxyphenyl)-1-piperazinyl]pentyl]-6-nitro-1H-benz[de]isoquinoline-1,3(2H)-dione
  参考文献：
  名称：

  Synthesis and Characterization of Environment-Sensitive Fluorescent Ligands for Human 5-HT_1A Receptors with 1-Arylpiperazine Structure

  摘要：

  A series of "long-chain" 1-(2-methoxyphenyl)piperzine derivatives containing an environment-sensitive fluorescent moiety (4-amino-1,8-naphthalimide, 4-dimethylaminophthalimide, dansyl) was synthesized. The compounds displayed very high to moderate 5-HT1A receptor affinity and good fluorescence properties. 6-Amino-2-[5-[4-(2-methoxyphenyl)-1-piperazinyl]pentyl]-1H-benz[de]isoquinoline-1,3(2H)-dione (4) combined very high 5-HT1A receptor affinity (K-i = 0.67 nM), high fluorescence emission in CHCl3, and undetectable fluorescence emission in aqueous solution. It was evaluated for its ability to visualize 5-HT1A receptors overexpressed in CHO cells by fluorescence microscopy.

  DOI：

  10.1021/jm900706d

文献信息

• Synthesis and Characterization of Environment-Sensitive Fluorescent Ligands for Human 5-HT_1A Receptors with 1-Arylpiperazine Structure
  作者：Enza Lacivita、Marcello Leopoldo、Anna Carmela Masotti、Carmela Inglese、Francesco Berardi、Roberto Perrone、Sourav Ganguly、Md Jafurulla、Amitabha Chattopadhyay

  DOI：10.1021/jm900706d

  日期：2009.12.10

  A series of "long-chain" 1-(2-methoxyphenyl)piperzine derivatives containing an environment-sensitive fluorescent moiety (4-amino-1,8-naphthalimide, 4-dimethylaminophthalimide, dansyl) was synthesized. The compounds displayed very high to moderate 5-HT1A receptor affinity and good fluorescence properties. 6-Amino-2-[5-[4-(2-methoxyphenyl)-1-piperazinyl]pentyl]-1H-benz[de]isoquinoline-1,3(2H)-dione (4) combined very high 5-HT1A receptor affinity (K-i = 0.67 nM), high fluorescence emission in CHCl3, and undetectable fluorescence emission in aqueous solution. It was evaluated for its ability to visualize 5-HT1A receptors overexpressed in CHO cells by fluorescence microscopy.