1419590-17-2Relevant academic research and scientific papers
Cyclopalladated benzophenone imines: Synthesis, cytotoxicity against human breast adenocarcinoma cell lines and DNA interaction
Albert, Joan,García, Silvia,Granell, Jaume,Llorca, Albert,Lovelle, María Victoria,Moreno, Virtudes,Presa, Andreu,Rodríguez, Laura,Quirante, Josefina,Calvis, Carme,Messeguer, Ramon,Badía, Josefa,Baldomà, Laura
, p. 289 - 296 (2013/03/14)
Treatment of benzophenone imine with the stoichiometric amount of Pd(OAc)2 in acetic acid at 60 °C produced the corresponding acetato-bridged five-membered ortho-cyclopalladated dimer [Pd{C 6H4CPhNH}(μ-OAc)]2 (1), which was isolated in pure form in a 79% yield. Reaction of 1 with an excess of LiCl in acetone gave rise to the corresponding chlorido-bridged cyclopalladated dimer [Pd{C 6H4CPhNH}(μ-Cl)]2 (2) in a 78% yield. Compounds 1-2 reacted with an excess of py-d5 or the stoichiometric amount of PPh3 to give the mononuclear compounds trans-N,L-[Pd{C 6H4CPhNH}(X)(L)] [3 (X = OAc, L = py-d5); 4 (X = Cl, L = py-d5); 5 (X = OAc, L = PPh3) and 6 (X = Cl, L = PPh3)]. Compounds 2-3 were prepared in CDCl3/py-d 5 solution and were studied by 1H NMR, but were not isolated. In contrast, compounds 5-6 were prepared in acetone and were isolated in pure form in 43 and 79% yields, respectively. Compounds 1, 2, 5 and 6 were characterized by elemental analyses, mass spectrometry, IR, NMR and electronic spectroscopy. Compounds 1, 2, 5 and 6 showed high antiproliferative activity against MDA-MB231 and MCF7 human breast cancer cell lines, especially, compounds 5-6. These two latter compounds presented greater antiproliferative activity than cisplatin and produced IC50 values in the range 1-5 μM. The interaction of compounds 1, 2, 5 and 6 with DNA was also studied by the DNA electrophoretic migration, DNA-ethidium bromide fluorescence quenching and viscometry techniques.
