1-[(6-fluoro-2-naphthyl)methyl]piperidin-4-ol | 403479-31-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1-[(6-fluoro-2-naphthyl)methyl]piperidin-4-ol
• 英文别名: 1-[(6-Fluoro-2-naphthalenyl)methyl]-4-piperidinol；1-[(6-fluoronaphthalen-2-yl)methyl]piperidin-4-ol
• CAS: 403479-31-2
• 化学式: C₁₆H₁₈FNO
• 分子量: 259.323
• InChiKey: OMAUTIVJEAILFJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  23.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-[(6-fluoro-2-naphthyl)methyl]piperidin-4-ol 、 异氰酸苯酯 以 甲苯 为溶剂， 反应 11.0h， 生成 [1-[(6-fluoronaphthalen-2-yl)methyl]piperidin-4-yl] N-phenylcarbamate
  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
• 作为产物：
  描述：

  4-羟基哌啶 、 2-bromomethyl-6-fluoronaphthalene 在 三乙胺 作用下， 以 氯仿 为溶剂， 反应 4.0h， 以84%的产率得到1-[(6-fluoro-2-naphthyl)methyl]piperidin-4-ol
  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