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Synthesis of Coumarin Derivatives as Inhibitors of Platelet Aggregation
Author(s) -
Chen YehLong,
Wang TaiChi,
Lee KuanHan,
Tzeng CherngChyi,
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.19960790308
Subject(s) - chemistry , coumarin , substituent , potency , platelet aggregation , stereochemistry , thrombin , arachidonic acid , platelet , lactone , platelet aggregation inhibitor , platelet activating factor , alkylation , in vitro , biochemistry , organic chemistry , aspirin , enzyme , catalysis , medicine , immunology , biology
In a search for the inhibitors of platelet aggregation, certain coumarin 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 4‐hydroxycoumarin ( 1 ) or naphthalen‐1‐ol via alkylation and Reformatsky ‐type condensation ( Schemes 1–3 ). Among them, 4‐[(2,3,4,5‐tetrahydro‐4‐methylidene‐5‐oxo‐2‐phenylfuran‐2‐yl)methoxy]‐2 H ‐1‐benzopyran‐2‐one ( 6b ) showed potent antiplatelet effects on AA‐ and PAF‐induced aggregation with IC 50 values of 8.21 and 103.67 m̈ M , respectively (see Tables 1 and 2 ). The antiplatelet potency of 6b against PAF‐induced aggregation could be further improved by introducing a proper substituent at the 2‐phenyl group of the lactone ring.