M. Reig, R. Bosque, M. Font-Bardía, C. Calvis, R. Messeguer, L. Baldomà, J. Badía, D. Velasco, C. López
文献索引:10.1016/j.jinorgbio.2018.03.008
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The synthesis and characterization of two hybrid N-methylated carbazole derivatives containing a thiazolyl or a thienyl ring on position 3 is reported. The thiazolyl derivative has been also characterized by X-Ray diffraction. The study of its reactivity in front of [MCl2(dmso)2] (M = Pd or Pt) or Na2[PdCl4] in methanol has allowed us to isolate and characterize its complexes. However, when the reactions were performed using the thienyl analogue, no evidences of the formation of any Pd(II) or Pt(II) complex were detected. Thus indicating that the latter is less prone to bind to the M(II) ions than its thiazolyl analogue. DFT and TD-DFT calculations have also been carried out in order to: a) rationalize the influence of the nature of the thiazolyl or thienyl group on the electronic delocalization and b) assign the bands detected in their electronic spectra. Molecular mechanics calculations show that the free rotation of the thiazolyl in relation to the carbazole requires a greater energy income than for its thienyl analogue. Comparative studies of the cytotoxic activity of the new ligands and the metal complexes on colon (HCT116) and two breast (MDA-MB231 and MCF7) cancer cell lines are also reported. In order to get additional information on mode of action of the new products, comparative studies on their potential ability to: a) modify the electrophoretic mobility of pBluescript SK+ plasmid DNA and b) act as inhibitors of Topoisomerases I and IIα or cathepsin B have also been carried out.
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