On the coordination behaviour of diorganoselenium ligands based on amino and azole functionalities: silver(i) complexes with relevance for biological applications?

New Journal of Chemistry Pub Date: 2022-11-07 DOI: 10.1039/D2NJ04812D

Abstract

A series of novel silver(I) complexes of type [Ag(OTf)L] (L = RR′Se), namely [Ag(OTf)Se{C6H4(CH2NMe2)-2}(CH2Phtz)] (1), [Ag(OTf)Se{C6H4(CH2NEt2)-2}(CH2Phtz)] (2), [Ag(OTf)Se{C6H4[CH2N(CH2CH2)2O]-2}(CH2Phtz)] (3), [Ag(OTf)Se{C6H4(CH2NMe2)-2}(CH2CH2pz)] (4), [Ag(OTf)Se{C6H4(CH2NEt2)-2}(CH2CH2pz)] (5), [Ag(OTf)Se{C6H4[CH2N(CH2CH2)2O]-2}(CH2CH2pz)] (6), and [Ag(OTf)Se(CH2Phtz)2] (7), were obtained by reacting the diorganoselenides L1–L7 with AgOTf in a 1?:?1 molar ratio. The new ligand L7 and the Ag(I) complexes were characterized by multinuclear NMR spectroscopy (1H, 13C{1H}, 19F{1H}, and 77Se{1H}), ESI+ mass spectrometry, elemental analysis, IR spectroscopy and molar conductivity. The molecular structures of complexes 2, 3, 7 and the hydrolysis product [Ag(OTf)2Se{C6H4[CH2N(H)(CH2CH2)2O]-2}(CH2CH2pz)]2 (6a) were determined by single-crystal X-ray diffraction. The metal complexes behave as 1?:?1 electrolytes in solution, but in the solid state the OTf group is coordinated to silver. The diorganoselenides show different coordination patterns, i.e. a κ2N,N′-κSe coordination mode in the monomeric species 2 and 3, while in the dimeric species 7 and 6a the ligands are coordinated in a μ-(1κN:2κN′)-1,2κ2Se and a μ-(1κSe:2κN) fashion, respectively. The in vitro antiproliferative activity of selected compounds was investigated and the results show that the silver(I) complexes have promising activity against the murine melanoma B16.F10 cells.

Graphical abstract: On the coordination behaviour of diorganoselenium ligands based on amino and azole functionalities: silver(i) complexes with relevance for biological applications
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