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Amide Coupling Reaction for the Synthesis of Bispyridine-based Ligands and Their Complexation to Platinum as Dinuclear Anticancer Agents
Published on: May 28, 2014
Crystal structures of three platinacyclic complexes bearing isopropyl eugenoxyacetate and pyridine derivatives
Nguyen Thi Thanh Chi1, Pham Van Thong1, Luc Van Meervelt2
1Department of Chemistry, Hanoi National University of Education, 136 Xuan Thuy, Cau Giay, Hanoi, Vietnam.
Abstract:
Three new platinum(II) complexes bearing a eugenol and a pyridine derivative, namely (η2-2-allyl-4-meth-oxy-5-{[(propan-2-yl-oxy)carbon-yl]meth-oxy}phenyl-κC 1)chlorido-(pyridine-κN)platinum(II), [Pt(C15H19O4)Cl(C5H5N)], (I), (η2-2-allyl-4-meth-oxy-5-{[(propan-2-yl-oxy)carbon-yl]meth-oxy}phenyl-κC 1)chlorido-(4-methyl-pyridine-κN)platinum(II), [Pt(C15H19O4)Cl(C6H7N)], (II), and (η2-2-allyl-4-meth-oxy-5-{[(propan-2-yl-oxy)carbon-yl]meth-oxy}phenyl-κC 1)chlorido(pyridine-4-carb-oxy-lic acid-κN)platinum(II), [Pt(C15H19O4)Cl(C6H5NO2)], (III), have been synthesized and further characterized by single-crystal X-ray diffraction. The PtII atoms exhibit the usual distorted square-planar coordination and are surrounded by one Cl atom, one N atom, and a C atom and C=C double bond of the eugenol ligand. The donor N atom of the pyridine ligand occupies a cis position with respect to the double bond. Complexes (I) and (II) crystallize isomorphously in space group P and display a similar crystal packing characterized by C-H⋯O hydrogen bonding, C-H⋯π and π-π inter-actions. However, the presence of the additional methyl group in the 4-methyl-pyridine ligand in (II) disturbs the π-π inter-actions. The crystal packing of (III) is characterized by O-H⋯O hydrogen bonding, resulting in the formation of chains of mol-ecules connected in a head-to-tail fashion and running in the [101] direction. The IC50 values for the HepG2 and KB cell lines are 150.9, 122.3 µM for (I) and 138.9, 93.2 µM for (II), respectively.
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