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  • Title: Novel derivatives of methyl and ethyl 2-(4-oxo-8-aryl-2H-3,4,6,7-tetrahydroimidazo[2,1-c][1,2,4]triazin-3-yl)acetates from biologically active 1-aryl-2-hydrazinoimidazolines: synthesis, crystal structure and antiproliferative activity.
    Author: Sztanke K, Rzymowska J, Niemczyk M, Dybała I, Kozioł AE.
    Journal: Eur J Med Chem; 2006 Dec; 41(12):1373-84. PubMed ID: 16996655.
    Abstract:
    The 1-aryl-2-hydrazinoimidazolines (2a-h) were directly obtained from appropriate 1-aryl-2-methylthioimidazolines (1a-h) by condensation reaction with hydrazine hydrate. Antimicrobial activities of two 1-aryl-2-hydrazinoimidazolines (2b and 2e) are presented. Their chemical structures were confirmed by IR, (1)H NMR, EI-MS and elemental analysis. The susceptibility of Gram-positive and Gram-negative bacterial strains, mould and yeast-like fungi strains to synthesized compounds and the MIC values against two reference strains of bacteria were determined. The strongest antibacterial activity for compound 2b in relation to reference Gram-negative Escherichia coli ATCC 25922 bacterial strain with minimal inhibitory concentration (MIC) value of 3.91micro g mL(-1) was found. Compound 2b showed superior activity (MIC) to ampicillin and comparable to chloramphenicol. A novel compound 2e was found to be effective against E. coli ATCC 25922 and Staphylococcus aureus ATCC 25923 at concentrations of 7.81micro g mL(-1) and 15.62micro g mL(-1), respectively. Compound 2e revealed antibacterial activity against E. coli ATCC 25922, superior to ampicillin and inferior to chloramphenicol. Against S. aureus ATCC 25923 strain tested, compound 2e demonstrated MIC value inferior to ampicillin and chloramphenicol. Moreover, the synthesis, crystal structure and antiproliferative activity of novel derivatives of methyl and ethyl 2-(4-oxo-8-aryl-2H-3,4,6,7-tetrahydroimidazo[2,1-c][1,2,4]triazin-3-yl)acetates (3a-f and 3g-j) are presented. These compounds were obtained from 1-aryl-2-hydrazinoimidazolines (2a-f) by the addition and cyclization reactions with fumaric acid esters. Molecular structures of these compounds were confirmed by elemental analysis, IR, (1)H NMR, (13)C NMR, EI-MS and by X-ray crystallography (for 3g). The tested imidazotriazines 3e, 3i and 3j exhibited anticancer activities towards the following cancer cells: LS180 (ECACC 87021202, human Caucasian colon adenocarcinoma cells), SiHa (ECACC 85060701, uterus cancer cells), and T47D (ECACC 85102201, human breast carcinoma cells). Compounds 3i and 3j having comparable GI values (above 50%) towards uterus cancer cell line (SiHa) at both examined concentrations (10micro g mL(-1) and 50micro g mL(-1)) were found to be the most effective against this cancer cell line; their GI factors were 53%, 51% and 62%, 55%, respectively, in both examined concentrations (10micro g mL(-1) and 50micro g mL(-1)). Furthermore, the distinctly marked lower cytotoxicity of tested imidazotriazines 3i and 3j against normal cell lines (HSF, human skin fibroblast cells and Vero African Green Monkey Kidney cells, GMK clone) and almost 2-times higher against the majority of cancer cell lines was confirmed.
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