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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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Two potential bioactive pyrimidine-5-carbonitrile derivatives have been synthesized and characterized by spectroscopic techniques ( ~(1) H 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–H?C 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–H?O hydrogen bond motif. Moreover, the structures of 1 and 2 display 1D isostructurality and molecular chains stabilize by intermolecular N–H?O and N–H?N 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–H?O hydrogen bonds, other non-covalent interactions are closed-shell in nature. A strong and linear N–H?O 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 and Staphylococcus 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，其特征在于光谱技术（〜（1）H和〜（13）C-NMR），并且在低温下通过单晶X射线衍射阐明三维结构（ 160 k）。在两个结构中，分子构象被涉及噻吩和苯基环的氰基和Ch的分子内C-H 2 C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，两个结构使用常见的N-H？O氢键基序。此外，通过分子间N-H 2 O和N-H氢键稳定1d和2显示1d isostr发生的结构和分子链。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-H 2 O氢键外，其他非共价相互作用本质上是封闭的。强且线性的N-H·O氢键显示共用和闭合壳相互作用之间的中间键合性。分子对接分析表明，两种化合物对来自人和金黄色葡萄球菌的二氢酚酸还原酶（DHFR）酶的潜在抑制作用。

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