1-methyl-4-(3',4'-dihydroxyphenyl)-1,2,3,6-tetrahydropyridine hydrobromide | 94427-32-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 1-methyl-4-(3',4'-dihydroxyphenyl)-1,2,3,6-tetrahydropyridine hydrobromide
• CAS: 94427-32-4
• 化学式: BrH*C₁₂H₁₅NO₂
• 分子量: 286.169
• InChiKey: JRRRPUFIMIWNSH-UHFFFAOYSA-N

反应信息

• 作为产物：
  描述：

  2-Methoxy-4-(1-methyl-1,2,3,6-tetrahydro-pyridin-4-yl)-phenol; hydrobromide 在 氢溴酸 作用下， 以 溶剂黄146 为溶剂， 反应 2.0h， 以86%的产率得到1-methyl-4-(3',4'-dihydroxyphenyl)-1,2,3,6-tetrahydropyridine hydrobromide
  参考文献：
  名称：

  Synthesis and dihydropteridine reductase inhibitory effects of potential metabolites of the neurotoxin 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine

  摘要：

  1-Methyl-4-phenyl-1,2,3,6-tetrahydropyridine (MPTP) is a nigrostriatal neurotoxin which can cause irreversible parkinsonism in humans and primates by selective destruction of neurons in the substantia nigra. It is possible that MPTP could be metabolized by hydroxylation of the phenyl ring and/or aromatization of its nitrogen-containing ring. Hydroxylated derivatives of 4-phenyl-1,2,3,6-tetrahydropyridine, 4-phenylpiperidine, and 4-phenylpyridine were synthesized and tested in vitro as inhibitors of dihydropteridine reductase (DHPR) from human liver and rat striatal synaptosomes. It was found that all hydroxy derivatives were about 100-10 000 times more inhibitory than MPTP to DHPR. The inhibitory potency of the hydroxylated derivatives increased with the number of hydroxyl substitutions present on the phenyl ring (catechol greater than phenol) and with oxidation of the nitrogen-containing ring (pyridine greater than tetrahydropyridine greater than piperidine).

  DOI：

  10.1021/jm00381a009