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Antiplatelet α‐Methylidene‐γ‐butyrolactones: Synthesis and evaluation of quinoline, flavone, and xanthone derivatives
Author(s) -
Wang TaiChi,
Chen YehLong,
Tzeng CherngChyi,
Liou ShorongShii,
Chang YaLing,
Teng CheMing
Publication year - 1996
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19960790612
Subject(s) - chemistry , xanthone , coumarin , quinoline , stereochemistry , arachidonic acid , alkylation , organic chemistry , catalysis , enzyme
As a continuation of our previous studies on the synthesis and antiplatelet activity of coumarin derivatives of α‐methylidene‐γ‐butyrolactones, certain quinoline, flavone, and xanthone derivatives were synthesized and evaluated for antiplatelet activity against thrombin (Thr)‐, arachidonic acid (AA)‐, collagen (Col)‐, and platelet‐activating factor (PAF)‐induced aggregation in washed rabbit platelets. These compounds were synthesized from quinolin‐8‐ol, flavon‐7‐ol, and xanthon‐3‐ol, respectively, via alkylation and Reformatsky ‐type condensation ( Schemes 1–3 ). By the comparison with comparison with coumarin α‐methylidene‐γ‐butyrolactone 3a , flavone and xanthone derivatives, 3b and 3c , respectively, are more selective in which only AA‐ and collagen‐induced aggregation are strongly inhibited. Most of the quinoline derivatives ( 9a–e ) exhibited broad‐spectrum antiplatelet activities.