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Issue 39, 2018
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Influence of the substituent on the phosphine ligand in novel rhenium(I) aldehydes. Synthesis, computational studies and first insights into the antiproliferative activity

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Abstract

Cyrhetrenyl aldehyde derivatives [(η5-C5H4CHO)Re(CO)2PR3] with R = methyl (Me, 2a), phenyl (Ph, 2b), and cyclohexyl (Cy, 2c) were synthesized by a photochemical reaction from the starting material [(η5-C5H4CHO)Re(CO)3] (1) and the corresponding phosphines. The complexes were fully characterized by FT-IR, 1H, 13C and 31P NMR spectroscopy, elemental analysis and mass spectrometry. The molecular structures of 2a–c have also been determined. Electronic structure calculations by TD-DFT and electrochemical studies are in sound agreement with the effect of the substitution of one carbonyl group by a phosphine ligand. Additionally, the antiproliferative activity of complexes 1 and 2a–c was studied on the human cancer cell lines HT-29 and PT-45 using an MTT assay. Out of all new compounds, only the triphenylphosphine derivative 2b exhibited pronounced cytotoxic effects on both cell lines, being ca. 1.5 times more potent than cisplatin.

Graphical abstract: Influence of the substituent on the phosphine ligand in novel rhenium(i) aldehydes. Synthesis, computational studies and first insights into the antiproliferative activity

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Publication details

The article was received on 02 Aug 2018, accepted on 03 Sep 2018 and first published on 07 Sep 2018


Article type: Paper
DOI: 10.1039/C8DT03160F
Citation: Dalton Trans., 2018,47, 13861-13869
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    Influence of the substituent on the phosphine ligand in novel rhenium(I) aldehydes. Synthesis, computational studies and first insights into the antiproliferative activity

    M. Muñoz-Osses, D. Siegmund, A. Gómez, F. Godoy, A. Fierro, L. Llanos, D. Aravena and N. Metzler-Nolte, Dalton Trans., 2018, 47, 13861
    DOI: 10.1039/C8DT03160F

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