1-ethyl-4-phenyl-1,2,3,6-tetrahydropyridine hydrochloride | 13314-64-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 1-ethyl-4-phenyl-1,2,3,6-tetrahydropyridine hydrochloride
• 英文别名: 1-Aethyl-4-phenyl-1,2,3,6-tetrahydro-pyridin; Hydrochlorid
• CAS: 13314-64-2
• 化学式: C₁₃H₁₇N*ClH
• 分子量: 223.746
• InChiKey: GYPDOUWUYGBMLN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.22
• 重原子数：
  15.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  3.24
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为产物：
  描述：

  1-乙基-4-苯基吡啶鎓碘化物 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 0.17h， 以30 mg的产率得到1-ethyl-4-phenyl-1,2,3,6-tetrahydropyridine hydrochloride
  参考文献：
  名称：

  Cytotoxicity of 1-Amino-4-phenyl-1,2,3,6-tetrahydropyridine and 1-Amino-4-phenylpyridinium Ion, 1-Amino Analogues of MPTP and MPP⁺, to Clonal Pheochromocytoma PC12 Cells

  摘要：

  1-Methyl-4-phenyl-1,2,3,6-tetrahydropyridine (MPTP) induces parkinsonism in humans after its oxidation into 1-methyl-4-phenylpyridinium ion (MPP+) by type B monoamine oxidase. The l-amino analogues of MPTP and MPP+, 1-amino-4-phenyl-1,2,3,6-tetrahydropyridine (APTP) and 1-amino-4-phenylpyridinium ion (APP(+)), were synthesized, and their cyto toxicity to clonal pheochromocytoma PC12 cells was examined using a tetrazolium formazan assay. After incubation for 48 and 72 h, both APP(+) and APTP were found to be cytotoxic to PC12 cells, whereas with the N-methyl analogues, only MPP+, but not MPTP, was cytotoxic. The cytotoxicity of APTP increased with incubation time and equaled that of MPP+ after 72 h. It was found that APTP was oxidized to APP(+) by type A monoamine oxidase in PC12 cells, suggesting that APP(+) itself may damage the cells. In addition to APTP and APP(+), N-amino analogues of N-methylisoquinolines and related derivatives were also synthesized and examined for their cytotoxicity to PC12 cells.

  DOI：

  10.1021/tx980032o

文献信息

• Cytotoxicity of 1-Amino-4-phenyl-1,2,3,6-tetrahydropyridine and 1-Amino-4-phenylpyridinium Ion, 1-Amino Analogues of MPTP and MPP⁺, to Clonal Pheochromocytoma PC12 Cells
  作者：Kohfuku Kohda、Yasuhiro Noda、Shinsuke Aoyama、Michi Umeda、Tomoe Sumino、Toyo Kaiya、Wakako Maruyama、Makoto Naoi

  DOI：10.1021/tx980032o

  日期：1998.11.1

  1-Methyl-4-phenyl-1,2,3,6-tetrahydropyridine (MPTP) induces parkinsonism in humans after its oxidation into 1-methyl-4-phenylpyridinium ion (MPP+) by type B monoamine oxidase. The l-amino analogues of MPTP and MPP+, 1-amino-4-phenyl-1,2,3,6-tetrahydropyridine (APTP) and 1-amino-4-phenylpyridinium ion (APP(+)), were synthesized, and their cyto toxicity to clonal pheochromocytoma PC12 cells was examined using a tetrazolium formazan assay. After incubation for 48 and 72 h, both APP(+) and APTP were found to be cytotoxic to PC12 cells, whereas with the N-methyl analogues, only MPP+, but not MPTP, was cytotoxic. The cytotoxicity of APTP increased with incubation time and equaled that of MPP+ after 72 h. It was found that APTP was oxidized to APP(+) by type A monoamine oxidase in PC12 cells, suggesting that APP(+) itself may damage the cells. In addition to APTP and APP(+), N-amino analogues of N-methylisoquinolines and related derivatives were also synthesized and examined for their cytotoxicity to PC12 cells.