N-[1-(6-Fluoro-naphthalen-2-ylmethyl)-piperidin-4-yl]-benzamide

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: N-[1-(6-Fluoro-naphthalen-2-ylmethyl)-piperidin-4-yl]-benzamide
• 英文别名: N-{1-[(6-fluoro-2-naphthyl)methyl]piperidin-4-yl}benzamide；N-[1-[(6-fluoronaphthalen-2-yl)methyl]piperidin-4-yl]benzamide
• 化学式: C₂₃H₂₃FN₂O
• 分子量: 362.447
• InChiKey: KMIVFOQFRIPVDV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  27
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  32.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-[1-(6-Fluoro-naphthalen-2-ylmethyl)-piperidin-4-yl]-benzamide 、 碘甲烷 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 以47%的产率得到N-[1-[(6-fluoronaphthalen-2-yl)methyl]piperidin-4-yl]-N-methylbenzamide
  参考文献：
  名称：

  Synthesis and structure–activity relationships of N-{1-[(6-fluoro-2-naphthyl)methyl]piperidin-4-yl}benzamide derivatives as novel CCR3 antagonists

  摘要：

  A novel class of potent CCR3 receptor antagonists were designed and synthesized starting from N-1-[(6-fluoro-2-naphthyl)methyl]piperidin-4-yl}benzamide (1),which was found by subjecting our chemical library to high throughput screening (HTS). The CCR3 inhibitory activity of the synthesized compounds against eotaxin-induced Ca2+ influx was evaluated using CCR3-expressing preB cells. Systematic chemical modifications of I revealed that the 6-fluoro-2-naphthylmethyl moiety was essential for CCR3 inhibitory activity in this new series of CCR3 antagonists. Further structural modifications of the benzamide and piperidine moieties of 1 led to the identification of N-{8-[(6-fluoro-2-naphthyl)methyl]-8-azabicyclo[3.2.1]oct-3- yl} biphenyl-2-carboxamide (31) as a potent CCR3 antagonist with an IC50 value of 0.020 mu M. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2007.10.003