6-[2-hydroxy-3-[methyl-[2-(N-methylanilino)ethyl]amino]propoxy]-1H-quinolin-2-one | 128667-82-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 6-[2-hydroxy-3-[methyl-[2-(N-methylanilino)ethyl]amino]propoxy]-1H-quinolin-2-one
• CAS: 128667-82-3
• 化学式: C₂₂H₂₇N₃O₃
• 分子量: 381.475
• InChiKey: TZWMYWKHPKRONH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  28
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  65
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  N,N'-dimethyl-N-phenyl-1,2-ethanediamine 、 6-(2,3-epoxypropoxy)-2(1H)-quinolinone 以 甲醇 为溶剂， 反应 3.0h， 生成 6-[2-hydroxy-3-[methyl-[2-(N-methylanilino)ethyl]amino]propoxy]-1H-quinolin-2-one
  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

• Carbostyril derivatives as phosphodiesterase inhibitors
  申请人：OTSUKA PHARMACEUTICAL CO., LTD.

  公开号：EP0647447A1

  公开（公告）日：1995-04-12

  A pharmaceutical preparation comprising at least one compound selected from the group consisting of carbostyril derivatives having the general formula: wherein R¹ is hydrogen or a lower alkyl group optionally having hydroxy group as a substituent; R² is a phenyl(lower alkyl) group optionally having 1 to 3 substituents selected from the group consisting of a lower alkoxy group and a halogen atom on the phenyl ring, pyridyl(lower alkyl) group, or a group of the formula -A-NR³R⁴ (wherein A is a lower alkylene group, R³ and R⁴ are the same or different and represent a lower alkyl group or phenyl group), and a salt thereof, which is useful as an agent for treating thrombosis, more particularly, as an agent for inhibiting platelet aggregation, an agent for platelet aggregate dissociation, an ameliorant of cerebral circulation and a phosphodiesterase inhibitor.

  一种药物制剂，包含至少一种选自具有通式的羧甲吡啶衍生物的化合物： 其中 R¹ 是氢或可选择具有羟基作为取代基的低级烷基；R² 是苯基（低级烷基）基团，可任选具有 1 至 3 个取代基，这些取代基可从苯基环上的低级烷氧基和卤原子、吡啶基（低级烷基）基团或式 -A-NR³R⁴ 的基团组成的组中选出（其中 A 是低级亚烷基、R³和R⁴相同或不同，代表低级烷基或苯基）及其盐，可用作治疗血栓的药物，特别是用作抑制血小板聚集的药物、血小板聚集解离剂、脑循环改善剂和磷酸二酯酶抑制剂。
• Carbostyril derivatives as anti-thrombotic agents
  申请人：OTSUKA PHARMACEUTICAL CO., LTD.

  公开号：EP0531548B1

  公开（公告）日：1995-09-27
• US5401754A
  申请人：——

  公开号：US5401754A

  公开（公告）日：1995-03-28
• US5532253A
  申请人：——

  公开号：US5532253A

  公开（公告）日：1996-07-02
• Novel positive inotropic agents: synthesis and biological activities of 6-(3-amino-2-hydroxypropoxy)-2(1H)-quinolinone derivatives
  作者：Takafumi Fujioka、Shuji Teramoto、Toyoki Mori、Tetsumi Hosokawa、Takumi Sumida、Michiaki Tominaga、Youichi Yabuuchi

  DOI：10.1021/jm00098a003

  日期：1992.10

  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.