2-<(cyanoacetyl)amino>-5-<3-(N-methyl-N-benzylamino)-2-hydroxypropoxy>benzaldehyde ethylene acetal | 143268-78-4

• 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: 2-<(cyanoacetyl)amino>-5-<3-(N-methyl-N-benzylamino)-2-hydroxypropoxy>benzaldehyde ethylene acetal
• 英文别名: N-[4-[3-[benzyl(methyl)amino]-2-hydroxypropoxy]-2-(1,3-dioxolan-2-yl)phenyl]-2-cyanoacetamide
• CAS: 143268-78-4
• 化学式: C₂₃H₂₇N₃O₅
• 分子量: 425.484
• InChiKey: KLVQFLQBDPAVEJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  31
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  104
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2-<(cyanoacetyl)amino>-5-<3-(N-methyl-N-benzylamino)-2-hydroxypropoxy>benzaldehyde ethylene acetal 在 盐酸 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以58.8%的产率得到6-[3-(Benzyl-methyl-amino)-2-hydroxy-propoxy]-2-oxo-1,2-dihydro-quinoline-3-carbonitrile
  参考文献：
  名称：

  Novel positive inotropic agents: synthesis and biological activities of 6-(3-amino-2-hydroxypropoxy)-2(1H)-quinolinone derivatives

  摘要：

  A series of 6-(3-amino-2-hydroxypropoxy)-2(1H)-quinolinones has been synthesized and evaluated for positive inotropic activity on the canine heart. Some of these derivatives have a potent activity with none or negative chronotropic effect in isolated, blood-perfused dog heart preparations. They also display a high selectivity for positive inotropic effect over chronotropic and vasodilatory effects in anesthetized dogs. (+/-)-6-[2-Hydroxy-3-[(3-methoxybenzyl)amino]propoxy]-2(1H)-quinolinone (39) and (+/-)-6-[3-(3,4-dimethoxybenzyl)amino]-2-hydroxypropoxy]-2(1H)-quinolinone (40) were further investigated in conscious dogs. After iv administration, they did not affect heart rate or mean blood pressure at the dose producing a 50% increase in the peak of the first derivative of the left ventricular pressure. The compounds (39,OPC-18750, and 40,OPC-18790) are the most promising agents with desirable biological activities, and now are currently undergoing clinical evaluation.

  DOI：

  10.1021/jm00098a003
• 作为产物：
  描述：

  5-(2,3-epoxypropoxy)-2-nitrobenzaldehyde ethylene acetal 在 palladium on activated charcoal 氢气 、 三乙胺 作用下， 以 甲醇 、 乙酸乙酯 为溶剂， 25.0 ℃ 、101.33 kPa 条件下， 反应 3.0h， 生成 2-<(cyanoacetyl)amino>-5-<3-(N-methyl-N-benzylamino)-2-hydroxypropoxy>benzaldehyde ethylene acetal
  参考文献：
  名称：

  Novel positive inotropic agents: synthesis and biological activities of 6-(3-amino-2-hydroxypropoxy)-2(1H)-quinolinone derivatives

  摘要：

  A series of 6-(3-amino-2-hydroxypropoxy)-2(1H)-quinolinones has been synthesized and evaluated for positive inotropic activity on the canine heart. Some of these derivatives have a potent activity with none or negative chronotropic effect in isolated, blood-perfused dog heart preparations. They also display a high selectivity for positive inotropic effect over chronotropic and vasodilatory effects in anesthetized dogs. (+/-)-6-[2-Hydroxy-3-[(3-methoxybenzyl)amino]propoxy]-2(1H)-quinolinone (39) and (+/-)-6-[3-(3,4-dimethoxybenzyl)amino]-2-hydroxypropoxy]-2(1H)-quinolinone (40) were further investigated in conscious dogs. After iv administration, they did not affect heart rate or mean blood pressure at the dose producing a 50% increase in the peak of the first derivative of the left ventricular pressure. The compounds (39,OPC-18750, and 40,OPC-18790) are the most promising agents with desirable biological activities, and now are currently undergoing clinical evaluation.

  DOI：

  10.1021/jm00098a003