3-(1-(2-aminoethyl)-1,2,3,6-tetrahydropyridin-4-yl)benzonitrile | 1574730-70-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3-(1-(2-aminoethyl)-1,2,3,6-tetrahydropyridin-4-yl)benzonitrile
• CAS: 1574730-70-3
• 化学式: C₁₄H₁₇N₃
• 分子量: 227.309
• InChiKey: LJHSYMUSSWCIGI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.61
• 重原子数：
  17.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  53.05
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  3-(1-(2-aminoethyl)-1,2,3,6-tetrahydropyridin-4-yl)benzonitrile 在 三乙酰氧基硼氢化钠 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 生成 3-(1-(2-((3-isopropylisoxazol-5-yl)methylamino)ethyl)-1,2,3,6-tetrahydropyridin-4-yl)benzonitrile
  参考文献：
  名称：

  Synthesis and biological evaluation of 1-(isoxazol-5-ylmethylaminoethyl)-4-phenyl tetrahydropyridine and piperidine derivatives as potent T-type calcium channel blockers with antinociceptive effect in a neuropathic pain model

  摘要：

  New tetrahydropyridinyl and piperidinyl ethylamine derivatives were designed with hypothetical mapping on pharmacophore model generated from ligand-based virtual screening. The designed compounds were synthesized, and their inhibitory activities on T-type calcium channel were assayed using FDSS and patch-clamp assay. Among them, compounds 7b and 10b showed potent T-type calcium current blocking activity against Ca(v)3.1 (alpha(1G)) and Ca(v)3.2 (alpha(1H)) channel simultaneously. With hERG and pharmacokinetics studies, compounds 7b and 10b were evaluated for the antinociceptive effect on rat model of neuropathic pain. They were significantly effective in decreasing the pain responses to mechanical and cold allodynia induced by spinal nerve ligation. These results suggest that modulation of alpha(1G) and am subtype T-type calcium channels may provide a promising approach for the treatment of neuropathic pain. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.12.056
• 作为产物：
  描述：

  3-(1-(2-(1,3-dioxoisoindolin-2-yl)ethyl)-1,2,3,6-tetrahydropyridin-4-yl)benzonitrile 在 一水合肼 作用下， 以 乙醇 为溶剂， 反应 2.0h， 以96%的产率得到3-(1-(2-aminoethyl)-1,2,3,6-tetrahydropyridin-4-yl)benzonitrile
  参考文献：
  名称：

  Synthesis and biological evaluation of 1-(isoxazol-5-ylmethylaminoethyl)-4-phenyl tetrahydropyridine and piperidine derivatives as potent T-type calcium channel blockers with antinociceptive effect in a neuropathic pain model

  摘要：

  New tetrahydropyridinyl and piperidinyl ethylamine derivatives were designed with hypothetical mapping on pharmacophore model generated from ligand-based virtual screening. The designed compounds were synthesized, and their inhibitory activities on T-type calcium channel were assayed using FDSS and patch-clamp assay. Among them, compounds 7b and 10b showed potent T-type calcium current blocking activity against Ca(v)3.1 (alpha(1G)) and Ca(v)3.2 (alpha(1H)) channel simultaneously. With hERG and pharmacokinetics studies, compounds 7b and 10b were evaluated for the antinociceptive effect on rat model of neuropathic pain. They were significantly effective in decreasing the pain responses to mechanical and cold allodynia induced by spinal nerve ligation. These results suggest that modulation of alpha(1G) and am subtype T-type calcium channels may provide a promising approach for the treatment of neuropathic pain. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.12.056