2014
DOI: 10.1007/s00044-014-1284-6
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Synthesis and in vitro antiplatelet aggregation screening of novel fluorinated diethyl-2-(benzylthio)-2,3-dihydro-1H-imidazole-4,5-dicarboxylate derivatives

Abstract: Seven fluorinated derivatives of diethyl-2-(benzylthio)-2,3-dihydro-1H-imidazole-4,5-dicarboxylate (a-g) as well as a nitro and chloro derivative (h-i) were prepared in five steps from glycine, ethyl formate, diethyl oxalate, potassium thiocyanate and substituted benzyl bromides. The structures of the synthesised compounds were elucidated and verified using 1 H, 13 C and 2D NMR spectroscopy where appropriate. The synthesised compounds exhibited concentration dependent antiplatelet aggregation activity on both … Show more

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Cited by 3 publications
(5 citation statements)
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References 28 publications
(27 reference statements)
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“…13 C­{ 1 H} NMR (101 MHz,DMSO) δ: 167.6, 61.6, 14.0. Spectroscopic data obtained are consistent with the data reported in the literature …”
Section: Methodssupporting
confidence: 91%
See 1 more Smart Citation
“…13 C­{ 1 H} NMR (101 MHz,DMSO) δ: 167.6, 61.6, 14.0. Spectroscopic data obtained are consistent with the data reported in the literature …”
Section: Methodssupporting
confidence: 91%
“…Spectroscopic data obtained are consistent with the data reported in the literature. 42 (4-Aminopiperidin-1-yl)(4-bromophenyl)methanone Hydrochloride (5o). Following GP3 to give the corresponding product as a white solid (62 mg, 97%).…”
Section: N-((6-methoxy-22-dimethyltetrahydrofuro[34-d][13]dioxol-4-yl...mentioning
confidence: 99%
“…Among the compounds, 4‐NO 2 ‐substituted and 4‐F‐substituted compounds exhibited the good activity with the thrombin‐induced assay and in the ADP‐induced platelet aggregation assay. 4‐NO 2 and 4‐F compounds exhibited the highest activity from the tested compounds with IC 50 values of 1.06 and 1.20 mM for the thrombin‐induced assay and 18.57 and 12.91 mM in the ADP‐induced platelet aggregation assay, respectively .…”
Section: Various Reaction Schemesmentioning
confidence: 99%
“…A series of fluorinated imidazole‐2‐thiones were prepared by Momin et al. that exhibited concentration‐dependent antiplatelet aggregation activity against thrombin‐ and ADP‐induced platelet aggregation …”
Section: Introductionmentioning
confidence: 99%
“…[9] As eries of fluorinated imidazole-2-thiones were prepared by Momin et al that exhibited concentrationdependenta ntiplatelet aggregation activity against thrombinand ADP-induced plateleta ggregation. [10] Ar eview of compounds with antiplatelet aggregation activity reveals that ah ydrazone moiety plays ap harmacophore role in many of these compounds.C helucci et al reported drugs hybridized with an N-acyl hydrazone subunitt hat showeda ntiplatelet and antithrombotic activities. [11] To deschini et al reported as eries of 2-pyridylhydrazones in 1998 with moderate inhibitory activity against arachidonic acid (AA).…”
Section: Introductionmentioning
confidence: 99%