Karle J M, Karle I L
Department of Pharmacology, Walter Reed Army Institute of Research, Washington, DC 20307-5100.
Acta Crystallogr C. 1988 Sep 15;44 ( Pt 9):1605-8. doi: 10.1107/s0108270188004652.
N4-(7-Chloro-4-quinolinyl)-N',N'-diethyl-1,4-pentanediamine bis(dihydrogenphosphate) dihydrate, C18H28ClN2+(3).2H2PO-4-2H2O, Mr = 551.8, monoclinic, P2(1)/c, a = 9.830 (2), b = 16.879 (3), c = 15.783 (4) A, beta = 105.51 (2) degrees, V = 2523.2 A3, Z = 4, Dx = 1.452 g cm-3, Mo K alpha, lambda = 0.71073 A, mu = 2.78 cm-1, F(000) = 1168, room temperature, final R = 5.5% for 2431 reflections with [F0] greater than 3 sigma. The chloroquine molecule is a dication with a hydrogen atom from each of the phosphate moieties residing on the quinoline and the terminal chain nitrogen atoms. Neighboring phosphate chains are bridged by chloroquine molecules via hydrogen bonding. Each hydrogen atom on each nitrogen atom, on each phosphate oxygen atom, and in each water molecule participates in hydrogen bonding. The helical manner in which the side chains of the chloroquine molecules wrap around phosphate chains and the stacking interval of the quinoline rings between the phosphate groups may be indicative of the interaction of chloroquine molecules with cellular constituents important to antimalarial action.
N4-(7-氯-4-喹啉基)-N',N'-二乙基-1,4-戊二胺双(磷酸二氢盐)二水合物，C18H28ClN2+(3).2H2PO4-2H2O，Mr = 551.8，单斜晶系，P2(1)/c，a = 9.830(2)，b = 16.879(3)，c = 15.783(4) Å，β = 105.51(2)°，V = 2523.2 Å3，Z = 4，Dx = 1.452 g cm-3，钼Kα，λ = 0.71073 Å，μ = 2.78 cm-1，F(000) = 1168，室温，对于2431个[F0]大于3σ的反射，最终R = 5.5%。氯喹分子是一种双阳离子，每个磷酸基团上的一个氢原子位于喹啉和末端链氮原子上。相邻的磷酸链通过氯喹分子通过氢键桥连。每个氮原子、每个磷酸氧原子和每个水分子上的每个氢原子都参与氢键形成。氯喹分子的侧链围绕磷酸链的螺旋方式以及磷酸基团之间喹啉环的堆积间隔可能表明氯喹分子与对抗疟作用重要的细胞成分之间的相互作用。
