Synthesis and evaluation of 2-{[(2-oxo-1H-quinolin-8-yl)oxy]methyl}- substituted α-metylidene-γ-butyrolactones
Journal
Helvetica Chimica Acta
Journal Volume
80
Journal Issue
4
Pages
1161-1168
Date Issued
1997
Author(s)
Abstract
Abstract O ‐Alkylation of 8‐hydroxy‐1 H ‐quinolin‐2‐one ( 1 ) afforded 8‐(2‐oxopropoxy)‐1 H ‐quinolin‐2‐one ( 2 ) which was immediately cyclized to form the tricyclic 2,3‐dihydro‐3‐hydroxy‐3‐methyl‐5 H ‐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]‐1 H ‐quinolin‐2‐one ( 4 ). Its counterparts 7a – f , Ph‐substituted at C(2) of the furan ring, were obtained from 1 via 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, Ca 2+ ‐induced vasoconstriction and was more active than most of its Ph‐substituted counterparts against norepinephrine‐induced vasoconstrictions.
SDGs
Type
journal article