4-(3',4'-dimethoxyphenyl)-1,2,3,6-tetrahydropyridine | 94427-39-1

• 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: 4-(3',4'-dimethoxyphenyl)-1,2,3,6-tetrahydropyridine
• 英文别名: 4-(3,4-Dimethoxyphenyl)-1,2,3,6-tetrahydropyridine
• CAS: 94427-39-1
• 化学式: C₁₃H₁₇NO₂
• mdl: MFCD11128350
• 分子量: 219.283
• InChiKey: LBRPLHNBPFDAHO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.384
• 拓扑面积：
  30.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-(3',4'-dimethoxyphenyl)-1,2,3,6-tetrahydropyridine 在 palladium on activated charcoal 作用下， 以 邻二甲苯 为溶剂， 反应 12.0h， 生成 4-(3,4-dimethoxyphenyl)pyridine
  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 、 potassium carbonate 作用下， 以 甲醇 、 水 、 溶剂黄146 、 丙酮 为溶剂， 反应 53.0h， 生成 4-(3',4'-dimethoxyphenyl)-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

• [EN] SUBSTITUTED AMINOQUINOLONES AS DGKALPHA INHIBITORS FOR IMMUNE ACTIVATION<br/>[FR] AMINOQUINOLONES SUBSTITUÉES EN TANT QU'INHIBITEURS DE DGKALPHA POUR ACTIVATION IMMUNITAIRE
  申请人：BAYER AG

  公开号：WO2021105117A1

  公开（公告）日：2021-06-03

  The present invention covers aminoquinolone compounds of general formula (I), in which R1, R2, R3, R4, R5, R6, R7, R8 and n are as defined herein, methods of preparing said compounds, intermediate compounds useful for preparing said compounds, pharmaceutical compositions and combinations comprising said compounds and the use of said compounds for manufacturing pharmaceutical compositions for the treatment and/or prophylaxis of diseases, in particular of diacylglycerol kinase alpha regulated disorders, as a sole agent or in combination with other active ingredients.

  本发明涵盖了一般式(I)的氨基喹啉酮化合物，其中R1、R2、R3、R4、R5、R6、R7、R8和n如本文所定义，制备所述化合物的方法，用于制备所述化合物的中间化合物，包括所述化合物的药物组合物和组合物，以及利用所述化合物制造用于治疗和/或预防疾病的药物组合物，特别是二酰基甘油激酶α调节性疾病，作为唯一药剂或与其他活性成分组合使用。
• Teirahydropyridine derivatives
  申请人：Shionogi & Co., Ltd.

  公开号：US05149817A1

  公开（公告）日：1992-09-22

  The present invention relates to tetrahydropyridine derivatives which have high affinity and specificity to .sigma. receptors, whereby these compounds are thought to be effective for treatment of some psychoses.

  本发明涉及对σ受体具有高亲和力和特异性的四氢吡啶衍生物，因此认为这些化合物对于治疗某些精神病是有效的。
• Tetrahydropyridine derivatives
  申请人：Shionogi & Co., Ltd.

  公开号：US05410058A1

  公开（公告）日：1995-04-25

  The compounds of the present invention relates to tetrahydropyridine derivatives and have high affinity and specificity to .sigma. receptors, whereby these are thought to be effective for some psychoses.

  本发明的化合物涉及四氢吡啶衍生物，具有高亲和力和特异性对σ受体，因此被认为对某些精神病有效。
• Novel tetrahydropyridine derivatives
  申请人：SHIONOGI SEIYAKU KABUSHIKI KAISHA trading under the name of SHIONOGI & CO. LTD.

  公开号：EP0445701A1

  公开（公告）日：1991-09-11

  The compounds of the present invention relates to tetrahydropyridine derivatives and have high affinity and specificity to σ receptors, whereby these are thought to be effective for some psychoses.

  本发明的化合物与四氢吡啶衍生物有关，对 σ 受体具有高亲和力和特异性，因此被认为对某些精神病有效。
• BROSSI, A.;GESSNER, W.;RONG-SEN, SHEN;ABELL, C. W., SYMP. CHEM. HETEROCYCL. COMPOUNDS (8TH) AND NUCL. ACID. COMPONENTS (6TH) +
  作者：BROSSI, A.、GESSNER, W.、RONG-SEN, SHEN、ABELL, C. W.

  DOI：——

  日期：——