1-acetyl-4-(3',4'-dihydroxyphenyl)-1,2,3,6-tetrahydropyridine | 94427-36-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 1-acetyl-4-(3',4'-dihydroxyphenyl)-1,2,3,6-tetrahydropyridine
• 英文别名: 1,2,3,6-Tetrahydropyridine, 1-acetyl-4-[4,5-dihydroxyphenyl]-；1-[4-(3,4-dihydroxyphenyl)-3,6-dihydro-2H-pyridin-1-yl]ethanone
• CAS: 94427-36-8
• 化学式: C₁₃H₁₅NO₃
• 分子量: 233.267
• InChiKey: UMFUUSYHSYHHNV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  60.8
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-acetyl-4-(3',4'-dihydroxyphenyl)-1,2,3,6-tetrahydropyridine 在 盐酸 作用下， 反应 2.0h， 以72%的产率得到4-(3',4'-dihydroxyphenyl)-1,2,3,6-tetrahydropyridine hydrochloride
  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
• 作为产物：
  描述：

  4,4-哌啶二醇 在 吡啶 、 盐酸 、 三溴化硼 、 potassium carbonate 作用下， 以 甲醇 、 氯仿 、 水 、 溶剂黄146 为溶剂， 反应 48.5h， 生成 1-acetyl-4-(3',4'-dihydroxyphenyl)-1,2,3,6-tetrahydropyridine
  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

文献信息

• GESSNER, W.;BROSSI, A.;SHEN, RONG-SEN;ABELL, C. W., J. MED. CHEM., 1985, 28, N 3, 311-317
  作者：GESSNER, W.、BROSSI, A.、SHEN, RONG-SEN、ABELL, C. W.

  DOI：——

  日期：——
• EP0730451A4
  申请人：——

  公开号：EP0730451A4

  公开（公告）日：2001-11-28
• BLOCKING UTILIZATION OF TETRAHYDROBIOPTERIN TO BLOCK INDUCTION OF NITRIC OXIDE SYNTHESIS
  申请人：CORNELL RESEARCH FOUNDATION, INC.

  公开号：EP0730451A1

  公开（公告）日：1996-09-11
• US5502050A
  申请人：——

  公开号：US5502050A

  公开（公告）日：1996-03-26
• US5874433A
  申请人：——

  公开号：US5874433A

  公开（公告）日：1999-02-23