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首页> 外文期刊>RSC Advances >Quantitative analysis of hydrogen and chalcogen bonds in two pyrimidine-5-carbonitrile derivatives, potential DHFR inhibitors: an integrated crystallographic and theoretical study
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Quantitative analysis of hydrogen and chalcogen bonds in two pyrimidine-5-carbonitrile derivatives, potential DHFR inhibitors: an integrated crystallographic and theoretical study

机译：两种嘧啶-5-腈衍生物中氢和硫致胶的定量分析，潜在的DHFR抑制剂：综合晶体和理论研究

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摘要

Two potential bioactive pyrimidine-5-carbonitrile derivatives have been synthesized and characterized by spectroscopic techniques (H-1 and(13)C-NMR) and the three dimensional structures were elucidated by single crystal X-ray diffraction at low temperature (160 K). In both structures, the molecular conformation is locked by an intramolecular C-HMIDLINE HORIZONTAL ELLIPSISC interaction involving the cyano and CH of the thiophene and phenyl rings. The intermolecular interactions were analyzed in a qualitative manner based on the Hirshfeld surface and 2D-fingerprint plots. The results suggest that the phenyl and thiophene moieties have an effect on the crystal packing. For instance, the chalcogen bonds are only preferred in the thiophene derivative. However, both structures uses a common N-HMIDLINE HORIZONTAL ELLIPSISO hydrogen bond motif. Moreover, the structures of1and2display 1D isostructurality and molecular chains stabilize by intermolecular N-HMIDLINE HORIZONTAL ELLIPSISO and N-HMIDLINE HORIZONTAL ELLIPSISN hydrogen bonds. The nature and extent of different non-covalent interactions were further characterized by the topological parameters derived from the quantum theory of atoms-in-molecules approach. This analysis indicates that apart from N-HMIDLINE HORIZONTAL ELLIPSISO hydrogen bonds, other non-covalent interactions are closed-shell in nature. A strong and linear N-HMIDLINE HORIZONTAL ELLIPSISO hydrogen bond shows intermediate bonding character between shared and closed-shell interactions. The molecular docking analysis suggests that both compounds display potential inhibitory effect against the dihydrofolate reductase (DHFR) enzyme from humans andStaphylococcus aureus.
机译：已经合成了两个潜在的生物活性嘧啶-5-碳腈衍生物，并通过光谱技术（H-1和（13）C-NMR），通过低温下的单晶X射线衍射阐明三维结构（160 k） 。在两个结构中，分子构象被涉及氰基和苯基环的氰基和Ch的分子内C-Hmidline水平椭圆相互作用锁定。基于HIRSHFELD表面和2D指纹图以定性方式分析分子间相互作用。结果表明苯基和噻吩部分对晶体包装有影响。例如，硫代菌键仅在噻吩衍生物中优选。然而，两种结构使用常见的N-Hmidline水平椭圆iso氢键基序。此外，通过分子间N-Hmidline水平椭圆和N-Hmidline水平椭圆氢键稳定1ds2display 1d肌肤性和分子链的结构。通过源自原子分子方法的量子理论的拓扑参数，进一步表征了不同非共价相互作用的性质和程度。该分析表明，除了N- Hmidline水平椭圆形溶液中，其他非共价相互作用本质上是封闭的。强且线性的N-Hmidline水平椭圆溶液氢键显示共用和闭合壳相互作用之间的中间键合特性。分子对接分析表明，两种化合物都显示出对来自人和气球的二氢酚酸盐还原酶（DHFR）酶的潜在抑制作用。

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  • 来源
    《RSC Advances》 |2020年第60期|共12页
  • 作者

    Al-Wahaibi Lamya H.; Chakraborty Kushumita; Al-Shaalan Nora H.; Majeed Mohamed Yehya Annavi Syed; Blacque Olivier; Al-Mutairi Aamal A.; El-Emam Ali A.; Percino M. Judith; Thamotharan Subbiah;

  • 作者单位

    Princess Nourah Bint Abdulrahman Univ Coll Sci Dept Chem Riyadh 11671 Saudi Arabia;

    SASTRA Deemed Univ Sch Chem &

    Biotechnol Dept Bioinformat Biomol Crystallog Lab Thanjavur 613401 India;

    Princess Nourah Bint Abdulrahman Univ Coll Sci Dept Chem Riyadh 11671 Saudi Arabia;

    SASTRA Deemed Univ Sch Chem &

    Biotechnol Dept Bioinformat Biomol Crystallog Lab Thanjavur 613401 India;

    Univ Zurich Dept Chem Winterthurerstr 190 CH-8057 Zurich Switzerland;

    Imam Mohammad Ibn Saud Islamic Univ IMSIU Coll Sci Dept Chem Riyadh 11671 Saudi Arabia;

    Mansoura Univ Fac Pharm Dept Med Chem Mansoura 35516 Egypt;

    Benemerita Univ Autonoma Puebla Inst Ciencias Unidad Polimeros &

    Elect Organ Val3 Ecocampus Valsequillo Puebla 72960 Mexico;

    SASTRA Deemed Univ Sch Chem &

    Biotechnol Dept Bioinformat Biomol Crystallog Lab Thanjavur 613401 India;

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