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首页> 外文期刊>Crystal growth & design >Substituent Effects on the Patterns of Intermolecular Interactions of 3-Alkyl and 3-Cycloalkyl Derivatives of Phenytoin: A Crystallographic and Quantum-Chemical Study
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Substituent Effects on the Patterns of Intermolecular Interactions of 3-Alkyl and 3-Cycloalkyl Derivatives of Phenytoin: A Crystallographic and Quantum-Chemical Study

机译：取代物对苯妥英3-烷基和3-环烷基衍生物的分子间相互作用模式：晶体和量子化学研究

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摘要

A series of five derivatives of the anticonvulsant drug phenytoin was synthesized, and their crystal structures were determined. The relationship between the molecular and crystal structure of the investigated compounds was rationalized in the context of contribution of intermolecular interactions and supramolecular structural motifs. The conformational preferences were analyzed by comparing the rotational freedom of the phenyl groups in the investigated compounds with 5,5-diphenylhydantoins from the Cambridge Structural Database. With the exception of compound 3 bearing the cyclopropyl group, the crystal packing of the investigated compounds contains centrosymmetric dimers linked by paired N-H center dot center dot center dot O hydrogen bonds, which further self-organize through pairs of C-H center dot center dot center dot O interactions and a parallel interaction of two phenyl rings at a large offset into chains running along the c-axis. The principal feature of the crystal structure of compound 3 is formation of the chains by N-H center dot center dot center dot O hydrogen bonds and C-H center dot center dot center dot O and C-H center dot center dot center dot pi interactions. The coordination of phenytoin enables more rotational freedom for the phenyl groups. An emphasis was placed on docking of the investigated compounds into the voltage-gated ion channel in the open and closed state. The obtained results indicate that hydrogen bonding and hydrophobic interactions are dominant in stabilizing energetically favored orientations of the investigated compounds bound to the protein.
机译：合成了抗惊厥药物苯妥汀的一系列五种衍生物，并测定它们的晶体结构。所研究的化合物的分子和晶体结构之间的关系在分子间相互作用和超分子结构基序的贡献中合理化。通过将所研究的化合物中的苯基与来自剑桥结构数据库的5,5-二苯基氢丁香蛋白的苯基的旋转自由度进行比较来分析构象偏好。除了携带环丙基的化合物3外，所研究的化合物的晶体包装含有由配对的NH中心点中心点中心点O氢键连接的亚富二聚体，其进一步通过CH中心点中心点中心点进行了进一步自组织o相互作用和两个苯环的平行相互作用在沿着C轴线的大偏移中的两个苯环。化合物3的晶体结构的主要特征是N-H中心点中心点中心点O氢键和C-H中心点中心点中心点O和C-H中心点中心点中心点PI相互作用的形成链条。苯妥英的配位使苯基的旋转自由度具有更多的旋转自由度。将研究的化合物对接到打开和关闭状态下的电压门控离子通道上。所得结果表明，氢键和疏水相互作用在稳定对蛋白质结合的所研究化合物的能量最有利的取向方面是显着的。

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  • 来源
    《Crystal growth & design》 |2019年第4期|共12页
  • 作者

    Trisovic Nemanja; Radovanovic Lidija; Janjic Goran V.; Jelic Stefan T.; Rogan Jelena;

  • 作者单位

    Univ Belgrade Fac Technol &

    Met Karnegijeva 4 Belgrade 11000 Serbia;

    Univ Belgrade Fac Technol &

    Met Innovat Ctr Karnegijeva 4 Belgrade 11000 Serbia;

    Univ Belgrade Inst Chem Technol &

    Met Njegoseva 12 Belgrade 11000 Serbia;

    Univ Belgrade Inst Multidisciplinary Res Kneza Viseslava 1 Belgrade 11000 Serbia;

    Univ Belgrade Fac Technol &

    Met Karnegijeva 4 Belgrade 11000 Serbia;

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  • 正文语种 eng
  • 中图分类 晶体学;
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