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Synthesis, characterization and crystal structures of the tetrachlorocuprate and tetrabromocadmate salts of the antimalarial mefloquine

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Abstract

Two new compounds, bis (DL-erythro-α-2-piperydylium-2,8-bis(trifluoromethyl)-4-quinolinemethanol) tetrachlorocuprate(II) tetrahydrate [LH+]2[CuCl4]2−∙4H2O 1 [L = mefloquine] and bis(DL-erythro-α-2-piperydylium-2,8-bis(trifluoromethyl)-4-quinolinemethanol) tetrabromocadmate (II) bis(methanol) [LH+]2[CdBr4]2−·2CH3OH 2, have been synthesized and characterized by elemental analysis, 1H-NMR and IR spectroscopy. Single-crystal X-ray diffraction analysis of 1 showed the structure to be ionic with formula unit comprising two protonated monocationic mefloquine molecules of opposite chirality, a tetrachlorocuprate (II) anion and a complement of four water molecules, disordered over several sites. The crystals are orthorhombic, space group Pnma, a = 9.6975(1) Å, b = 29.5385(3) Å, c = 15.9423(1) Å, V = 4566.67(7) Å3, Z = 4. The formula unit of compound 2 comprises two protonated monocationic mefloquine molecules, a tetrabromocadmate(II) anion and two molecules of methanol. The crystals are orthorhombic, space group Fdd2, a = 17.2185(5) Å, b = 55.456(2) Å, c = 9.5140(3) Å, V = 9084.6(5) Å3, Z = 8. The mefloquine molecule is protonated at the piperidinyl N atom and extensive hydrogen bonding occurs in both crystal structures. The conformation of the mefloquine cation in 1 and 2 is very similar to that recently observed in other salts of the drug, confirming its relevance in the context of antimalarial action.

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Acknowledgments

We are grateful for financial support from the Science and Technology Education Post-Basic Project (Step B) and the University of Ilorin. We thank the University of Cape Town and the NRF (Pretoria) for research support.

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Authors and Affiliations

  1. Department of Chemistry, University of Ilorin, Ilorin, Nigeria

    Joshua A. Obaleye & Adedibu C. Tella

  2. Department of Chemistry, University of Cape Town, Rondebosch, 7701, South Africa

    Mino R. Caira

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  1. Joshua A. Obaleye
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  2. Mino R. Caira
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  3. Adedibu C. Tella
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Correspondence to Mino R. Caira.

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Obaleye, J.A., Caira, M.R. & Tella, A.C. Synthesis, characterization and crystal structures of the tetrachlorocuprate and tetrabromocadmate salts of the antimalarial mefloquine. Struct Chem 20, 859–868 (2009). https://doi.org/10.1007/s11224-009-9484-2

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