Antiplatelet activities of newly synthesized derivatives of piperlongumine.
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.
Park
Byeoung-Soo
BS
Institute of Ecological Phytochemistry, Hankyong National University, Ansung-City, Kyonggi-Do 456-749, Korea.
Son
Dong-Ju
DJ
Choi
Won-Sik
WS
Takeoka
Gary R
GR
Han
Sung Ok
SO
Kim
Tae-Wan
TW
Lee
Sung-Eun
SE
D000818:Animals; D004148:Dioxolanes / Q000737:chemistry / Q000494:pharmacology*; D066298:In Vitro Techniques; D008297:Male; D010975:Platelet Aggregation Inhibitors / Q000737:chemistry / Q000494:pharmacology*; D011817:Rabbits; D013057:Spectrum Analysis / Q000379:methods; D010881:Piperidones
D004148:Dioxolanes; D010975:Platelet Aggregation Inhibitors; C498077:piperlongumine; D010881:Piperidones