6-甲基-1,2,3,6-四氢吡啶 | 127382-80-3

• 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
• 中文名称: 6-甲基-1,2,3,6-四氢吡啶
• 英文名称: 6-methyl-1,2,3,6-tetrahydropyridine
• 英文别名: Pyridine, 1,2,5,6-tetrahydro-2-methyl-
• CAS: 127382-80-3
• 化学式: C₆H₁₁N
• mdl: MFCD19223252
• 分子量: 97.16
• InChiKey: JHSFOVBZJMTSJL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  7
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.666
• 拓扑面积：
  12
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  甲基碘化镁 、 1-甲基-4-苯基吡啶离子 以 乙醚 为溶剂， 反应 2.0h， 以38%的产率得到1,2-dimethyl-4-phenylpyridinium iodide
  参考文献：
  名称：

  In vivo intracerebral microdialysis studies in rats of MPP+ (1-methyl-4-phenylpyridinium) analogs and related charged species

  摘要：

  The in vivo dopaminergic neurotoxic properties of 45 MPTP and MPP+ analogues and related compounds were examined by an intrastriatal microdialysis assay in conscious rats. MPP(+)-like toxicity, as evidenced by the irreversible effects on DA release and enhancement of lactate formation, was observed with a variety of structural types although no compound was more toxic than MPP+. The following global structure-toxicity relationships could be derived: (1) only permanently charged compounds showed neurotoxic effects; (2) with the exception of amino groups, hydrophilic substituents abolished toxicity; (3) activity was enhanced by lipophilic groups although increased steric bulk around the nitrogen atom tended to decrease activity; (4) nonaromatic, quaternary systems (methiodide of MPTP, guanidinium derivatives) were only weakly toxic; and (5) certain bi- and tricyclic systems, including putative metabolites of potential endogenous MPTP-like compounds, were weakly toxic. The lack of toxic effects following perfusions with DA itself confirmed that MPTP dopaminergic neurotoxicity is not likely to be mediated by the MPP(+)-induced release of DA. With some interesting exceptions, these in vivo data correlate reasonably well with in vitro data on the nerve terminal uptake properties and the inhibitory effects on mitochondrial respiration of these compounds.

  DOI：

  10.1021/jm00170a029

文献信息

• In vivo intracerebral microdialysis studies in rats of MPP+ (1-methyl-4-phenylpyridinium) analogs and related charged species
  作者：Hans Rollema、E. Anne Johnson、Raymond G. Booth、Patricia Caldera、Peter Lampen、Stephen K. Youngster、Anthony J. Trevor、Noreen Naiman、Neal Castagnoli

  DOI：10.1021/jm00170a029

  日期：1990.8

  The in vivo dopaminergic neurotoxic properties of 45 MPTP and MPP+ analogues and related compounds were examined by an intrastriatal microdialysis assay in conscious rats. MPP(+)-like toxicity, as evidenced by the irreversible effects on DA release and enhancement of lactate formation, was observed with a variety of structural types although no compound was more toxic than MPP+. The following global structure-toxicity relationships could be derived: (1) only permanently charged compounds showed neurotoxic effects; (2) with the exception of amino groups, hydrophilic substituents abolished toxicity; (3) activity was enhanced by lipophilic groups although increased steric bulk around the nitrogen atom tended to decrease activity; (4) nonaromatic, quaternary systems (methiodide of MPTP, guanidinium derivatives) were only weakly toxic; and (5) certain bi- and tricyclic systems, including putative metabolites of potential endogenous MPTP-like compounds, were weakly toxic. The lack of toxic effects following perfusions with DA itself confirmed that MPTP dopaminergic neurotoxicity is not likely to be mediated by the MPP(+)-induced release of DA. With some interesting exceptions, these in vivo data correlate reasonably well with in vitro data on the nerve terminal uptake properties and the inhibitory effects on mitochondrial respiration of these compounds.