1-methyl-4-(1-naphthylvinyl)-2-(acetylimino)pyridine | 113009-60-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1-methyl-4-(1-naphthylvinyl)-2-(acetylimino)pyridine
• CAS: 113009-60-2
• 化学式: C₂₀H₁₈N₂O
• 分子量: 302.376
• InChiKey: UOAUHWYTLZUFBB-IOKZDYJBSA-N

反应信息

• 作为反应物：
  描述：

  1-methyl-4-(1-naphthylvinyl)-2-(acetylimino)pyridine 在 盐酸 作用下， 以 乙醚 为溶剂， 生成 (E)-4-(1-naphthylvinyl)-2-(acetylamino)pyridine methochloride
  参考文献：
  名称：

  Approaches to protection against nerve agent poisoning. (Naphthylvinyl)pyridine derivatives as potential antidotes

  摘要：

  Analogues of the potent inhibitor of choline acetyltransferase (CAT) (E)-4-(1-naphthylvinyl)pyridine methiodide were synthesized and evaluated for their ability to inhibit CAT and protect against nerve agent intoxication. Several compounds, notably (E)-1-(2-hydroxyethyl)-(1-naphthylvinyl)pyridinium bromide (3), (E)-1-methyl-4-(1-naphthylvinyl)-1,2,3,6-tetrahydropyridine hydrochloride (22), and (E)-1-methyl-4-(1-naphthylvinyl)piperidine hydrochloride (23), were found to afford significant protection against sarin in the mouse and against soman in the guinea pig. However, protection was apparently not related to CAT inhibition. Compound 23, our most effective compound in protecting against nerve agent, was without CAT inhibitory activity. Compound 22, which proved to be a potent CAT inhibitor, most likely owed this activity to being dehydrogenated back to the pyridinium quaternary salt by oxidative enzymes. Several of the (naphthylvinyl)pyridine quaternary salts, but not their tertiary amine analogues, were found to be effective in slowing the rate of aging of soman-inhibited acetylcholinesterase. Ability to slow the rate of aging was enhanced by introduction of methoxy substituents on the aryl moiety whereas the aging rate was actually accelerated by chloro substituents. To date, our most effective compound in slowing the rate of aging, (E)-4-[(4-methoxy-1-naphthyl)vinyl]pyridine methochloride (6), did not provide significant protection against soman in the mouse.

  DOI：

  10.1021/jm00399a022
• 作为产物：
  描述：

  1-萘甲醛 在 哌啶 、 sodium hydroxide 作用下， 以 甲醇 为溶剂， 反应 16.0h， 生成 1-methyl-4-(1-naphthylvinyl)-2-(acetylimino)pyridine
  参考文献：
  名称：

  Approaches to protection against nerve agent poisoning. (Naphthylvinyl)pyridine derivatives as potential antidotes

  摘要：

  Analogues of the potent inhibitor of choline acetyltransferase (CAT) (E)-4-(1-naphthylvinyl)pyridine methiodide were synthesized and evaluated for their ability to inhibit CAT and protect against nerve agent intoxication. Several compounds, notably (E)-1-(2-hydroxyethyl)-(1-naphthylvinyl)pyridinium bromide (3), (E)-1-methyl-4-(1-naphthylvinyl)-1,2,3,6-tetrahydropyridine hydrochloride (22), and (E)-1-methyl-4-(1-naphthylvinyl)piperidine hydrochloride (23), were found to afford significant protection against sarin in the mouse and against soman in the guinea pig. However, protection was apparently not related to CAT inhibition. Compound 23, our most effective compound in protecting against nerve agent, was without CAT inhibitory activity. Compound 22, which proved to be a potent CAT inhibitor, most likely owed this activity to being dehydrogenated back to the pyridinium quaternary salt by oxidative enzymes. Several of the (naphthylvinyl)pyridine quaternary salts, but not their tertiary amine analogues, were found to be effective in slowing the rate of aging of soman-inhibited acetylcholinesterase. Ability to slow the rate of aging was enhanced by introduction of methoxy substituents on the aryl moiety whereas the aging rate was actually accelerated by chloro substituents. To date, our most effective compound in slowing the rate of aging, (E)-4-[(4-methoxy-1-naphthyl)vinyl]pyridine methochloride (6), did not provide significant protection against soman in the mouse.

  DOI：

  10.1021/jm00399a022