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Studies on anti-platelet agents. V. Synthesis and structure-activity relationship of 3-substituted 5,6-bis(4-methoxyphenyl)-1,2,4-triazines
The syntheses and structure-activity relationships of a series of 3-substituted 5,6-bis(4-methoxyphenyl)-1,2,4-triazines as anti-platelet agents based on cyclooxygenase (CO) inhibition are described. Of these compounds, 1-[5,6-bis(4-methoxyphenyl)-1,2,4-triazin-3-yl]carbonyl-4-methylpipera zine (10) exhibited potent CO inhibition in vitro (IC50 = 2.8 x 10-7 M) with vasodilatory activity (ED50 = 4.5 x 10-5 M). Compound 10 also showed potent ex vivo activities, completely preventing platelet aggregation induced by arachidonic acid and collagen at 6 h after oral administration of 3.2 and 1.0 mg/kg. The ex vivo potency of 10 is more than three times that of aspirin. Moreover, 10 demonstrated no gastrointestinal side effect in rats even at 100 mg/kg in spite of its potent CO inhibition activity, while aspirin, the most widely-used anti-platelet drug, showed gastrointestinal side effects in a dose-dependent manner (32, 100, and 320 mg/kg) in our study. These results suggested that 10 is a very attractive candidate for development as an anti-platelet drug since an aspirin-like anti-platelet agent, based on CO inhibition and being free from gastrointestinal side effects, is a major goal of thromboembolic research.
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Reference£º
Pyridazine – Wikipedia,
Pyridazine | C4H4N1021 – PubChem