Bicyclo[2.2.2]octenes represent a very diverse and challenging group of compounds, ranging from natural products to functional materials. They also represent a very synthetically useful class of compounds that have attracted the attention of numerous organic chemists. Here, we described an efficient, MW-assisted and ionic-liquid-catalyzed esterification of bicyclo[2.2.2]oct-7-ene-2,3,5,6-tetracarboxylic acid dianhydride derivatives into the corresponding tetraesters. The latter were subjected to a base-catalyzed isomerization reaction, which proceeded with the retention of symmetry. We have proven that the isomerization is controlled by the presence of the bridgehead amide group, but it does not take place in a stereoselective way if the benzamide group was N-methylated.
COBISS.SI-ID: 34968581
The aim of this work was to evaluate the preferential binding mode of 1-(2-picolyl)-4-phenyl-1H-1,2,3-triazole (ppt) on octahedral Ru complexes and to assess how it influences the antiproliferative (antitumor activity) activity of half-sandwich Ru coordination compounds. The 1,4-disubstituted 1,2,3-triazole ligand ppt was prepared by click chemistry and was investigated as novel chelating ligand for Ru(II) complexes. The preparation and structural characterization, mainly by NMR spectroscopy in solution and by X-Ray crystallography in the solid state, of four new Ru(II) complexes is reported. In all compounds ppt firmly binds to ruthenium in a bidentate fashion through the pyridyl nitrogen atom and the triazole N2, thus forming a puckered six-membered ring. The chemical behavior in aqueous solution of the complexes was studied by UV-Vis and NMR spectroscopy and compared to that of the previously described analogues in view of their potential antitumor activity. Compounds were tested in vitro for cytotoxic activity against two human cancer cell lines, one sensitive and one resistant to cisplatin, in comparison with cisplatin. One of the compounds was found to be more cytotoxic than cisplatin against human lung squamose carcinoma cell line (A-549).
COBISS.SI-ID: 34899461
We have shown that 4-nitro-substituted 1,3-diaryltriazenes with two additional electron-withdrawing groups are highly cytotoxic compounds. They were acylated at the triazene nitrogen to increase the solubility. N-acyltriazenes can be considered as prodrugs of non-acylated triazenes. The antiproliferative activity of new compounds depends on the type of the substituent introduced at the ortho position of the benzene rings (trifluoromethyl has the strongest influence). It was found that 3-acetyl-1,3-bis(4-nitro-2-chlorophenyl)triazene exhibited high cytotoxicity against different tumor cell lines including drug-resistant carcinoma cell lines and higher cytotoxicity against tumor cells as compared to normal cells.
COBISS.SI-ID: 34964997