

SYNTHESIS OF 2H-PYRANO[3,2-g]QUINOLIN-2-ONES CONTAINING A PYRIMIDINONE MOIETY AND CHARACTERIZATION OF THEIR ANTICOAGULANT ACTIVITY VIA INHIBITION OF BLOOD COAGULATION FACTORS Xa AND XIa

Abstract
The reactions of 7-hydroxy-1,2,2,4-tetramethylhydroquinoline-6-carbaldehydes with methyl 3-oxopentanedioate were used to synthesize 3-oxo-3-(6,8,8,9-tetramethyl-2-oxo-2H-pyrano[3,2-g]quinolin-3-yl)propanoates with various degrees of hydrogenation in the pyridine ring, the condensation of which with carboximidamides provided a series of new 6,8,8,9-tetramethyl-3-(6-oxo-1,6-dihydropyrimidin-4-yl)-2H-pyrano[3,2-g]quinolin-2-ones. It was found that some compounds of this class exhibited relatively high inhibitory activity against the blood coagulation factors Xа and XIa.
Keywords
carboximidamide; methyl 2-oxo-(2H-pyrano[3,2-g]quinolin-3-yl)propanoate; 3-(6-oxo-1,6-dihydro-4-pyrimidinyl)-2H-pyrano[3,2-g]quinolin-2-one; 3-oxopentanedioate; pyrano[3,2-g]quinoline; pyrimidine; factor Xa; factor XIa; molecular hybridization.
Latvian Institute of Organic Synthesis - Aizkraukles iela, 21, Riga, LV-1006, Latvia - hgs@osi.lv