C. Tzeng, Yeh‐long Chen, Chaojie Wang
Jun 30, 1997
Citations
0
Influential Citations
15
Citations
Journal
Helvetica Chimica Acta
Abstract
O-Alkylation of 8-hydroxy-1H-quinolin-2-one (1) afforded 8-(2-oxopropoxy)-1H-quinolin-2-one (2) which was immediately cyclized to form the tricyclic 2,3-dihydro-3-hydroxy-3-methyl-5H-pyrido[1,2,3-de][1,4]benzoxazine,-5-one (3). The Reformatsky-type condensation of 3 furnished antiplatelet 8-[(2,3,4,5-tetrahydro-2-methyl-4-methylidene-5-oxofuran-2-yl)melhoxy]-1H-quinolin-2-one (4). Its counterparts 7a–f, Ph-substituted at C(2) of the furan ring, were obtained from 1via alkylation and the Reformatsky-type condensation. Although compound 4 was less active against platelet aggregation than 7a–f, it was the only compound which exhibited significant inhibitory activity on high-K+ medium, Ca2+-induced vasoconstriction and was more active than most of its Ph-substituted counterparts against norepinephrine-induced vasoconstrictions.