N-(1-benzylpiperidin-4-yl)-3-nitrophenylacetamide | 208184-81-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: N-(1-benzylpiperidin-4-yl)-3-nitrophenylacetamide
• 英文别名: N-(1-Benzyl-piperidin-4-yl)-2-(3-nitro-phenyl)-acetamide；N-(1-benzylpiperidin-4-yl)-2-(3-nitrophenyl)acetamide
• CAS: 208184-81-0
• 化学式: C₂₀H₂₃N₃O₃
• 分子量: 353.421
• InChiKey: BCVXIEVBPYWULE-UHFFFAOYSA-N

物化性质

• 熔点：
  170-173 °C
• 沸点：
  576.6±50.0 °C(Predicted)
• 密度：
  1.23±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  78.2
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  4-氨基-1-苄基哌啶 、 3-硝基苯乙酸 在 N,N'-二环己基碳二亚胺 作用下， 生成 N-(1-benzylpiperidin-4-yl)-3-nitrophenylacetamide
  参考文献：
  名称：

  Synthesis and Quantitative Structure−Activity Relationships of N-(1-Benzylpiperidin-4-yl)phenylacetamides and Related Analogues as Potent and Selective σ₁ Receptor Ligands

  摘要：

  A series of N-(1-benzylpiperidin-4-yl)pherlylacetamide derivatives was synthesized and evaluated for affinity at or and oz receptors. Most of these compounds showed a high affinity for sigma(1) receptors and a low to moderate affinity for sigma(2) receptors. The unsubstituted compound N-(1-benzylpiperidin-4-yl)phenylacetamide, 1, displayed a high affinity and selectivity for sigma(1) receptors (K-i) values of 3.90 nM for sigma(1) receptors and 240 nM for sigma(2) receptors. The influence of substitutions on the phenylacetamide aromatic ring on binding at both the sigma(1) and sigma(2) receptor has been examined through Hansch-type quantitative structure-activity relationship (QSAR) studies. In general, all 3-substituted compounds, except for the OH group, had a higher affinity for both sigma(1) and sigma(2) receptors when compared with the corresponding 2- and 4-substituted analogues. The selectivity for sigma(1) receptors displayed a trend of 3 > 2 approximate to 4 for Cl, Pr, F, NO2, and OMe substituted analogues. Halogen substitution on the aromatic ring generally increased the affinity for sigma(2) receptors while maintaining a similar affinity for sigma(1) receptors. Substitution with electron-donating groups, such as OH, OMe, or NH2, resulted in weak or negligible affinity for sigma(2) receptors and a moderate affinity for sigma(1) receptors. The 2-fluoro-substituted analogue, 11, exhibited the highest selectivity for sigma(1) receptors among all compounds tested, with a K-i value of 3.56 nM for sigma(1) receptors and 667 nM for sigma(2) receptors. Compounds 1, 5, 9, 11, and 20 had no affinity for dopamine D-2 (IC50 > 10 000 nM) and D-3 (IC50 > 10 000 nM) receptors. The nanomolar binding affinity and high selectivity for sigma(1) receptors suggest that these compounds may be developed as potential radiotracers for positron emission tomography or single photon emission computerized tomography imaging studies.

  DOI：

  10.1021/jm980032l