8-[(2-methoxyethyl)amino]-3,3-dimethyl-6-[(4-methylphenyl)amino]-3,4-dihydro-1H-pyrano[3,4-c]pyridine-5-carbonitrile

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃吡啶类
• 英文名称: 8-[(2-methoxyethyl)amino]-3,3-dimethyl-6-[(4-methylphenyl)amino]-3,4-dihydro-1H-pyrano[3,4-c]pyridine-5-carbonitrile
• 英文别名: 8-(2-methoxyethylamino)-3,3-dimethyl-6-(4-methylanilino)-1,4-dihydropyrano[3,4-c]pyridine-5-carbonitrile
• 化学式: C₂₁H₂₆N₄O₂
• 分子量: 366.463
• InChiKey: VPHHKZBEWXRJBG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  27
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  79.2
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  C₁₉H₂₂N₃OS⁽¹⁺⁾*CH₃O₄S^(1-) 、 2-甲氧基乙胺 以 甲醇 为溶剂， 反应 2.0h， 以68%的产率得到8-[(2-methoxyethyl)amino]-3,3-dimethyl-6-[(4-methylphenyl)amino]-3,4-dihydro-1H-pyrano[3,4-c]pyridine-5-carbonitrile
  参考文献：
  名称：

  Synthesis and neurotropic activity of 6,8-diamino derivatives of pyrano[3,4-c]pyridines

  摘要：

  New diamino derivatives of pyrano[3,4-c]pyridines were synthesized by the pyridine ring recyclization. The presence of the intramolecular hydrogen bond in 6-[(4-methoxyphenyl)amino]-3,3-dimethyl8-methylamino-3,4-dihydro-1H-pyrano[3,4-c]pyridin-5-carbonitrile was identified by X-ray diffraction. A pharmacological study of the synthesized compounds was carried out in known tests, such as assay for antagonism induced by corazole subcutaneous injection and the open field test. The method of rotating rod was used to evaluate neurotoxicity. The diamino derivatives of pyrano[3,4-c]pyridines were found to possess neutrotropic properties. The synthesized compounds, as well as diazepam, prevent the occurrence of clonic seizures and clonic corazoleinduced convulsions in animals; however, they cause a behavior-depressing sedative effect.

  DOI：

  10.1134/s1068162016020102

文献信息

• Synthesis and neurotropic activity of 6,8-diamino derivatives of pyrano[3,4-c]pyridines
  作者：E. G. Paronikyan、Sh. Sh. Dashyan、I. A. Dzhagatspanyan、R. G. Paronikyan、I. M. Nazaryan、A. G. Akopyan、N. S. Minasyan、A. G. Ayvazyan、R. A. Tamazyan、E. V. Babaev

  DOI：10.1134/s1068162016020102

  日期：2016.3

  New diamino derivatives of pyrano[3,4-c]pyridines were synthesized by the pyridine ring recyclization. The presence of the intramolecular hydrogen bond in 6-[(4-methoxyphenyl)amino]-3,3-dimethyl8-methylamino-3,4-dihydro-1H-pyrano[3,4-c]pyridin-5-carbonitrile was identified by X-ray diffraction. A pharmacological study of the synthesized compounds was carried out in known tests, such as assay for antagonism induced by corazole subcutaneous injection and the open field test. The method of rotating rod was used to evaluate neurotoxicity. The diamino derivatives of pyrano[3,4-c]pyridines were found to possess neutrotropic properties. The synthesized compounds, as well as diazepam, prevent the occurrence of clonic seizures and clonic corazoleinduced convulsions in animals; however, they cause a behavior-depressing sedative effect.