Tutughamiarso Maya, Bolte Michael, Egert Ernst
Institut für Organische Chemie und Chemische Biologie, Goethe-Universität Frankfurt, Max-von-Laue-Strasse 7, 60438 Frankfurt am Main, Germany.
Acta Crystallogr C. 2009 Nov;65(Pt 11):o574-8. doi: 10.1107/S010827010903950X. Epub 2009 Oct 10.
In order to better understand the interaction between the pharmaceutically active compound 5-fluorocytosine [4-amino-5-fluoropyrimidin-2(1H)-one] and its receptor, hydrogen-bonded complexes with structurally similar bonding patterns have been investigated. During the cocrystallization screening, three new pseudopolymorphs of 5-fluorocytosine were obtained, namely 5-fluorocytosine dimethyl sulfoxide solvate, C(4)H(4)FN(3)O.C(2)H(6)OS, (I), 5-fluorocytosine dimethylacetamide hemisolvate, C(4)H(4)FN(3)O.0.5C(4)H(9)NO, (II), and 5-fluorocytosine hemihydrate, C(4)H(4)FN(3)O.0.5H(2)O, (III). Similar hydrogen-bond patterns are observed in all three crystal structures. The 5-fluorocytosine molecules form ribbons with repeated R(2)(2)(8) dimer interactions. These dimers are stabilized by N-H...N and N-H...O hydrogen bonds. The solvent molecules adopt similar positions with respect to 5-fluorocytosine. Depending on the hydrogen bonds formed by the solvent, the 5-fluorocytosine ribbons form layers or tubes. A database study was carried out to compare the hydrogen-bond pattern of compounds (I)-(III) with those of other (pseudo)polymorphs of 5-fluorocytosine.
为了更好地理解药用活性化合物5-氟胞嘧啶[4-氨基-5-氟嘧啶-2(1H)-酮]与其受体之间的相互作用，对具有结构相似键合模式的氢键复合物进行了研究。在共结晶筛选过程中，获得了5-氟胞嘧啶的三种新假多晶型物，即5-氟胞嘧啶二甲亚砜溶剂化物，C(4)H(4)FN(3)O.C(2)H(6)OS，(I)；5-氟胞嘧啶二甲基乙酰胺半溶剂化物，C(4)H(4)FN(3)O.0.5C(4)H(9)NO，(II)；以及5-氟胞嘧啶半水合物，C(4)H(4)FN(3)O.0.5H(2)O，(III)。在所有三种晶体结构中都观察到了相似的氢键模式。5-氟胞嘧啶分子通过重复的R(2)(2)(8)二聚体相互作用形成条带。这些二聚体通过N-H...N和N-H...O氢键得以稳定。溶剂分子相对于5-氟胞嘧啶采取相似的位置。根据溶剂形成的氢键，5-氟胞嘧啶条带形成层或管。进行了一项数据库研究，以比较化合物(I)-(III)与5-氟胞嘧啶其他(假)多晶型物的氢键模式。
