5-(2,3-epoxypropoxy)-2-nitrobenzaldehyde ethylene acetal | 112859-49-1

• 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: 5-(2,3-epoxypropoxy)-2-nitrobenzaldehyde ethylene acetal
• 英文别名: 2-[2-nitro-5-(oxiran-2-ylmethoxy)phenyl]-1,3-dioxolane
• CAS: 112859-49-1
• 化学式: C₁₂H₁₃NO₆
• 分子量: 267.238
• InChiKey: UHFXHJYDHIHZGM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  86
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  5-(2,3-epoxypropoxy)-2-nitrobenzaldehyde ethylene acetal 在 palladium on activated charcoal 氢气 作用下， 以 乙酸乙酯 为溶剂， 生成 2-(1,3-Dioxolan-2-yl)-4-(oxiran-2-ylmethoxy)aniline
  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-hydroxy-2-nitrobenzaldehyde ethylene acetal 、 环氧氯丙烷 在 potassium carbonate 作用下， 以 甲醇 为溶剂， 反应 20.0h， 以59.9%的产率得到5-(2,3-epoxypropoxy)-2-nitrobenzaldehyde 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

文献信息

• US4775674A
  申请人：——

  公开号：US4775674A

  公开（公告）日：1988-10-04