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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
Mixed natural arylolefin-quinoline platinum(II) complexes: synthesis, structural characterization and in vitro
Nguyen Thi Thanh Chi1, Pham Van Thong1, Truong Thi Cam Mai2
1Department of Chemistry, Hanoi National University of Education, 136 Xuan Thuy, Cau Giay, Hanoi, Vietnam.
Abstract:
Five new platinum(II) complexes bearing a eugenol and a quinoline derivative, namely [η2-4-allyl-2-methoxy-1-(propoxycarbonylmethoxy)benzene]-trans-dichlorido(quinoline-κN)platinum(II), [PtCl2(C15H20O4)(C9H7N)], (2), {η2-4-allyl-2-methoxy-1-[(propan-2-yloxy)carbonylmethoxy]benzene}-trans-dichlorido(quinoline-κN)platinum(II), [PtCl2(C15H19O4)(C9H7N)], (3), [η2-4-allyl-2-methoxy-1-(propoxycarbonylmethoxy)benzene]chlorido(quinolin-8-olato-κ2N,O)platinum(II), [Pt(C9H6NO)Cl(C15H20O4)], (4), {η2-4-allyl-2-methoxy-1-[(propan-2-yloxy)carbonylmethoxy]benzene}chlorido(quinolin-8-olato-κ2N,O)platinum(II), [Pt(C9H6NO)Cl(C15H20O4)], (5), and [η2-4-allyl-2-methoxy-1-(propoxycarbonylmethoxy)benzene]chlorido(quinolin-2-carboxylato-κ2N,O)platinum(II), [Pt(C10H6NO2)Cl(C15H20O4)], (6), have been synthesized and fully characterized spectroscopically. A single-crystal X-ray diffraction study was carried out for complexes (2) and (4)-(6). PrEug [or 4-allyl-2-methoxy-1-(propoxycarbonylmethoxy)benzene] in (2), (4) and (6), and iPrEug (the propan-2-yloxy analogue of PrEug) in (3) and (5) coordinate with PtII at the ethylenic double bond of the allyl group. In (2)-(6), the donor N atom of the amine group occupies a trans position with respect to the double bond. A comparison of the IC50 values of 0.38-29.23 µM for (2)-(6) with cisplatin, as well as other platinum(II) complexes, indicates an excellent in vitro cytotoxicity against the KB, LU, Hep-G2 and MCF-7 cancer cell lines, with the highest cytotoxic effect (IC50 = 0.38-1.99 µM) being for complexes (4) and (5) bearing a quinolin-8-olate ligand.
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