N-[(4-chlorophenyl)methyl]-3-[1-(4-fluorophenyl)indol-3-yl]-N-methylpropan-1-amine | 1092060-49-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: N-[(4-chlorophenyl)methyl]-3-[1-(4-fluorophenyl)indol-3-yl]-N-methylpropan-1-amine
• CAS: 1092060-49-5
• 化学式: C₂₅H₂₄ClFN₂
• 分子量: 406.93
• InChiKey: JLFYFIFBNZIHBD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  29
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  8.2
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  3-[1-(4-fluorophenyl)-1H-indol-3-yl]propyl-1-methanesulfonate 、 N-甲基-4-氯苄胺 在 potassium carbonate 作用下， 以 various solvent(s) 为溶剂， 反应 16.0h， 以52%的产率得到N-[(4-chlorophenyl)methyl]-3-[1-(4-fluorophenyl)indol-3-yl]-N-methylpropan-1-amine
  参考文献：
  名称：

  Substituted benzylaminoalkylindoles with preference for the σ2 binding site

  摘要：

  In the attempt to develop new sigma ligands we synthesized a series of N-benzyl-3-[1-(4-fluorophenyl)-1H-indol-3-yl]-N-methylpropan-1-amines and N-benzyl-4-[1-(4-fluorophenyl)-1H-indol-3-yl]-N-methylbutan-1-amines variously substituted on the phenyl ring. The displacement percentages of [H-3]-DTG and [H-3]-(+)-pentazocine determined in rat liver homogenates by these compounds at the fixed 100 nM concentration have been determined as a preliminary evaluation of their sigma(1) and sigma(2) affinity, respectively.The results suggested that the phenyl substituents may positively modulate, in comparison with the unsubstituted compound, the ability to displace [H-3]-DTG from sigma(2) sites, whereas the same phenyl substituents reduced the displacement percentages of [H-3]-(+)-pentazocine from sigma(1), sites. Some of these compounds were selected for radioligand binding assays. Compounds with a butylene intermediate chain displayed the greatest binding affinity for sigma(2) over sigma(1) receptors. The butylene derivative with 2,4-dimethyl substitution on the phenyl ring showed the greatest sigma(2) affinity (sigma K-2(i) = 5.9 nM) and an appreciable sigma(2) over sigma(1) selectivity (sigma K-1(i)/sigma K-2(i) = 22). The obtained results suggest that a butylene chain separating the indole moiety from variously substituted benzylamino groups may be required to their interaction with a hypothetical secondary sigma(2) binding site. (C) 2007 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2007.09.012

文献信息

• Substituted benzylaminoalkylindoles with preference for the σ2 binding site
  作者：Maria Grazia Mamolo、Daniele Zampieri、Caterina Zanette、Chiara Florio、Simona Collina、Mariangela Urbano、Ornella Azzolina、Luciano Vio

  DOI：10.1016/j.ejmech.2007.09.012

  日期：2008.10

  In the attempt to develop new sigma ligands we synthesized a series of N-benzyl-3-[1-(4-fluorophenyl)-1H-indol-3-yl]-N-methylpropan-1-amines and N-benzyl-4-[1-(4-fluorophenyl)-1H-indol-3-yl]-N-methylbutan-1-amines variously substituted on the phenyl ring. The displacement percentages of [H-3]-DTG and [H-3]-(+)-pentazocine determined in rat liver homogenates by these compounds at the fixed 100 nM concentration have been determined as a preliminary evaluation of their sigma(1) and sigma(2) affinity, respectively.The results suggested that the phenyl substituents may positively modulate, in comparison with the unsubstituted compound, the ability to displace [H-3]-DTG from sigma(2) sites, whereas the same phenyl substituents reduced the displacement percentages of [H-3]-(+)-pentazocine from sigma(1), sites. Some of these compounds were selected for radioligand binding assays. Compounds with a butylene intermediate chain displayed the greatest binding affinity for sigma(2) over sigma(1) receptors. The butylene derivative with 2,4-dimethyl substitution on the phenyl ring showed the greatest sigma(2) affinity (sigma K-2(i) = 5.9 nM) and an appreciable sigma(2) over sigma(1) selectivity (sigma K-1(i)/sigma K-2(i) = 22). The obtained results suggest that a butylene chain separating the indole moiety from variously substituted benzylamino groups may be required to their interaction with a hypothetical secondary sigma(2) binding site. (C) 2007 Elsevier Masson SAS. All rights reserved.