SYNTHESIS AND ABSOLUTE-CONFIGURATION OF THE ENANTIOMERS OF UORO-1-METHYL-3-(METHYLSULFINYL)-4(1H)-QUINOLINONE (FLOSEQUINAN)

Authors
MORITA S OHTSUBO K MATSUBARA J OHTANI T UCHIDA M KIDO M SHIMIZU T
Citation
S. Morita et al., SYNTHESIS AND ABSOLUTE-CONFIGURATION OF THE ENANTIOMERS OF UORO-1-METHYL-3-(METHYLSULFINYL)-4(1H)-QUINOLINONE (FLOSEQUINAN), Chemical and Pharmaceutical Bulletin, 42(10), 1994, pp. 2157-2160
Citations number
8
Categorie Soggetti
Pharmacology & Pharmacy",Chemistry
Journal title
Chemical and Pharmaceutical Bulletin → ACNP
ISSN journal
00092363
Volume
42
Issue
10
Year of publication
1994
Pages
2157 - 2160
Database
ISI
SICI code
0009-2363(1994)42:10<2157:SAAOTE>2.0.ZU;2-Z
Abstract
The enantiomers of uoro-1-methyl-3-(methylsulfinyl)-4(1H)-quinolinone [(+/-)-1, flosequinan], a new drug for the treatment of heart failure, were synthesized from the optically active (R)-alpha-methylbenzylamin e derivatives of quinoline. The key intermediates, (R)-alpha-methylben zylamine derivatives, were prepared by diastereomeric separation. The configuration of (+)-1 was assigned on the basis of an X-ray crystallo graphic analysis of the synthetic precursor (4a). The absolute configu ration was found to be (R)-(+)-1 and (S)-(-)-1.