Preparation and antiplatelet activity of glycidic acid derivatives |
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Authors: | Josef Jampílek Eliška Brojerová Martin Doležal Jiří Kuneš Daniel Jun |
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Institution: | (1) Zentiva, a.s., U Kabelovny 130, CZ-102 37 Prague, Czech Republic;(2) Faculty of Pharmacy in Hradec Králové, Charles University in Prague, Heyrovského 1203, CZ-500 05 Hradec Králové, Czech Republic;(3) Department of Toxicology, Faculty of Military Medicine, University of Defence, Třebešská 1575, CZ-500 01 Hradec Králové, Czech Republic |
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Abstract: | Arylalkanoic acid derivatives exhibit a variety of biological effects. In the current publication some of new glycidic acid
derivatives were prepared via the Darzens condensation. The synthetic approach, analytical and spectroscopic data of all newly
synthesized compounds are presented. The prepared compounds were evaluated as potential inhibitors of arachidonic acid-induced
platelet aggregation and their activity was compared with that of acetylsalicylic acid as the standard. (±)-Ethyl 3-{4-(4-methoxyphenyl)sulfanyl]phenyl}-3-methyl-cis-oxirane-2-carboxylate (IC50 = 0.07 mmol L−1) and (±)-3-{4-(4-methoxyphenyl)sulfanyl]phenyl}-3-methyl-cis-oxirane-2-carboxylic acid (IC50 = 0.06 mmol L−1) showed the highest antiplatelet activity against arachidonic acid-induced platelet aggregation comparable with the standard.
Structure-activity relationships between the chemical structure, lipophilicity, and the antiplatelet activity of the evaluated
compounds are discussed. |
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Keywords: | glycidic acid derivatives Darzens condensation geometric isomerism in vitro antiplatelet activity lipophilicity structure-activity relationships |
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