Display Settings:

Format

Send to:

Choose Destination

    Acta Crystallogr C. 2006 Feb;62(Pt 2):o53-7. Epub 2006 Jan 14.

    Three 4-aminoquinolines of antimalarial interest.

    Bourne SA, De Villiers K, Egan TJ.

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

    The structures of three compounds with potential antimalarial activity are reported. In N,N-diethyl-N'-(7-iodoquinolin-4-yl)ethane-1,2-diamine, C15H20IN3, (I), the molecules are linked into ribbons by N-H...N and C-H...N hydrogen bonds. In N-(7-bromoquinolin-4-yl)-N',N'-diethylethane-1,2-diamine dihydrate, C15H20BrN3.2H2O, (II), two aminoquinoline molecules and four water molecules form an R5(4)(13) hydrogen-bonded ring which links to its neighbours to form a T5(2) one-dimensional infinite tape with pendant hydrogen bonds to the aminoquinolines. The phosphate salt 7-chloro-4-[2-(diethylammonio)ethylamino]quinolinium bis(dihydrogenphosphate) phosphoric acid, C15H22ClN3(2+).2H2PO4-.H3PO4, (III), was prepared in order to establish the protonation sites of these compounds. The phosphate ions form a two-dimensional hydrogen-bonded sheet, while the aminoquinoline cations are linked to the phosphates by N-H...O hydrogen bonds from each of their three N atoms. While the conformation of the quinoline region hardly varies between (I), (II) and (III), the amino side chain is much more flexible and adopts a significantly different conformation in each case. Aromatic pi-pi stacking interactions are the only supramolecular interactions seen in all three structures.

    PMID: 16456284 [PubMed - indexed for MEDLINE]

    Supplemental Content

    Click here to read