Synthesis and Biological Activities of Optically Active 6-[3-(3, 4-Dimethoxybenzylamino)-2-hydroxypropoxy]-2(1H)-quinolinone (OPC-18790)

Synthesis and Biological Activities of Optically Active 6-[3-(3, 4-Dimethoxybenzylamino)-2-hydroxypropoxy]-2(1H)-quinolinone (OPC-18790)

The enanitomers 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)-qui...

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Veröffentlicht in:Chemical & pharmaceutical bulletin 1996/08/15, Vol.44(8), pp.1596-1598
Hauptverfasser: FUJIOKA, Takafumi, TERAMOTO, Shuji, TSUJIMI, Sachiko, TAKEMOTO, Kazumi, MORI, Toyoki, HOSOKAWA, Tetsumi, SUMIDA, Takumi, TOMINAGA, Michiaki, YABUUCHI, Youichi
Format: Artikel
Sprache:eng
Schlagworte:
2(1H)-quinolinone
Animals
Biological and medical sciences
cardiotonic agent
Cardiotonic agents
Cardiotonic Agents - chemical synthesis
Cardiotonic Agents - pharmacology
Cardiovascular system
Dogs
In Vitro Techniques
Medical sciences
Myocardial Contraction - drug effects
OPC-18790
optically active epichlorohydrin
Pharmacology. Drug treatments
positive inotropic activity
Quinolones - chemical synthesis
Quinolones - pharmacology
Stereoisomerism
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Zusammenfassung:The enanitomers 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.
ISSN:0009-2363
1347-5223
DOI:10.1248/cpb.44.1596