17810-04-7Relevant academic research and scientific papers
Synthesis and antiplatelet activity of new imidazole-4-carboxylic acid derivatives
Rehse, Klaus,Steege, Jens
, p. 539 - 547 (2007/10/03)
1-Arylalkyl-5-phenylsulfonamino-imidazole-4-carboxylic acid esters and their carboxamides with an additional secondary amino group were synthesized and identified as antiplatelet agents in a low micromolar range (Born-test, inducer collagen). To describe the mechanism of action more precisely the Born-test was carried out as well with ADP, adrenaline or PAF, respectively. In addition, two compounds were investigated for their COX-1 inhibitory activities. Provided the essential structural criteria are met i.e. amide group or ester, sulfonylamino rest, hydrophobic moieties, and a secondary amino function, slight structural modifications are able to shift the pattern of activity among the above platelet receptors. So, the ester 5c exhibits PAF antagonistic activity at IC 50 = 1 μM and COX-1 inhibition (IC50 = 0.4 μM). The carboxamide 6c shows ADP antagonistic properties (IC50 = 2 μM). Compound 6g is as well PAF antagonistic (IC50 = 4 μM) and a COX-1 inhibitor (IC50 = 1 μM). The derivative 6i shows a strong antiadrenergic (IC50 = 0.15 μM) and PAF antagonistic (IC 50 = 0.66 μM) effect.
