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Antiplatelet activities of newly synthesized derivatives of piperlongumine
Author(s) -
Park ByeoungSoo,
Son DongJu,
Choi WonSik,
Takeoka Gary R.,
Han Sung Ok,
Kim TaeWan,
Lee SungEun
Publication year - 2008
Publication title -
phytotherapy research
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.019
H-Index - 129
eISSN - 1099-1573
pISSN - 0951-418X
DOI - 10.1002/ptr.2432
Subject(s) - chemistry , stereochemistry , piperidine , alkaloid , arachidonic acid , thrombin , platelet , inhibitory postsynaptic potential , pharmacology , biochemistry , enzyme , medicine , immunology
Piperlongumine, a pyridone alkaloid isolated from Piper longum L., exhibited a potential inhibitory effect on washed rabbit platelet aggregation induced by collagen, arachidonic acid (AA) and platelet activating factor (PAF), without any inhibitory effect on that induced by thrombin. Piperlongumine was used as a lead compound for the synthesis of new antiplatelet agents. Seven synthetic compounds were newly synthesized from 3,4,5‐trimethoxycinnamic acid (TMCA). They were 1‐piperidin‐1‐yl‐3‐(3,4,5‐trimethoxy‐phenyl)prop‐2‐en‐1‐one (1′), 1‐morpholin‐4‐yl‐3‐(3,4,5‐trimethoxyphenyl)prop‐2‐en‐1‐one (2′), 1‐(3,5‐dimethylpiperidin‐1‐yl)‐3‐(3,4,5‐trimethoxyphenyl)prop‐2‐en‐1‐one (3′), 1‐(2‐methylpiperidin‐1‐yl)‐3‐(3,4,5‐tri‐methoxyphenyl)prop‐2‐en‐1‐one (4′), 1‐(3‐hydroxypiperidin‐1‐yl)‐3‐(3,4,5‐trimethoxyphenyl)‐ prop‐2‐en‐1‐one (5′), 1‐[3‐(3,4,5‐tri‐methoxyphenyl) acryloyl]‐piperidin‐2‐one (6′) and ethyl 1‐[3‐(3,4,5‐trimethoxyphenyl)‐acryloyl]piperidine‐4‐carboxylate (7′). Among those seven synthetic derivatives, 1‐(3,5‐dimethylpiperidin‐1‐yl)‐3‐(3,4,5‐trimethoxyphenyl)prop‐2‐en‐1‐one (3′) had the most inhibitory effect on platelet aggregation induced by collagen, AA and PAF. Copyright © 2008 John Wiley & Sons, Ltd.