128667-95-8

Usage

InChI:InChI=1/C21H24N2O5/c1-26-19-7-3-14(9-20(19)27-2)11-22-12-16(24)13-28-17-5-6-18-15(10-17)4-8-21(25)23-18/h3-10,16,22,24H,11-13H2,1-2H3,(H,23,25)

Upstream product

• 128668-82-6 6-((R)-3-Chloro-2-hydroxy-propoxy)-1H-quinolin-2-one 
• 5763-61-1 3,4-dimethoxybenzylamine 
• 128668-81-5 S-6-(3-chloro-2-hydroxypropoxy)carbostyril 
• 128668-84-8 6-(2,3-epoxypropoxy)-2(1H)-quinolinone 
• 19315-93-6 6-hydroxy-1H-quinolin-2-one 

Relevant academic research and scientific papers

Synthesis and biological activities of optically active 6-[3-(3,4- Dimethoxybenzylamino)-2-hydroxypropoxy]-2(1H)-quinolinone (OPC-18790)

The enantiomers of 6-[3-(3,4-dimethoxybenzylamino)-2-hydroxypropoxy]- 2(1H)-quinolinone (OPC-18790), a novel cardiotonic agent, were synthesized and evaluated for positive inotropic activity. The key intermediates, 2,3- epoxypropoxy derivatives, were obtained by the alkylation of 6-hydroxy- 2(1H)-quinolinone with optically active epichlorohydrin and subsequent ring closure. In an in vitro study, the (R)-(+)-isomer was about 10-fold more potent than the (s)-(-)-isomer.

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

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.