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Novel Fluorescent Benzothiazolyl-Coumarin Hybrids as Anti-SARS-COVID-2 Agents Supported by Molecular Docking Studies: Design, Synthesis, X-ray Crystal Structures, DFT, and TD-DFT/PCM Calculations
ACS Omega ( IF 3.7 ) Pub Date : 2023-05-23 , DOI: 10.1021/acsomega.3c01085 Amira E M Abdallah 1 , Samir A Abdel-Latif 1 , Galal H Elgemeie 1
ACS Omega ( IF 3.7 ) Pub Date : 2023-05-23 , DOI: 10.1021/acsomega.3c01085 Amira E M Abdallah 1 , Samir A Abdel-Latif 1 , Galal H Elgemeie 1
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This study revealed the design and preparation of new 3-(benzo[d]thiazol-2-yl)-2H-chromen-2-one derivatives 9a–h. The structures of the synthesized products were elucidated by their spectroscopic data and X-ray crystallography for compounds 9a and 9d. The prepared new compounds were measured for their fluorescence, and a good result indicated that the emission efficiency was decreased by increasing the electron-withdrawing groups from the unsubstituted compound 9a to the highly substituted derivative 9h (2 Br heavy atoms). On the other hand, the B3LYP/6-311G** theoretical level of theory was used to optimize the quantum mechanical calculations of the geometrical characteristics and energy of the novel compounds 9a–h under study. The electronic transition was investigated using the TD-DFT/PCM B3LYP approach, which uses time-dependent density functional calculations. Moreover, the compounds exhibited nonlinear optical properties (NLO) and a small HOMO–LUMO energy gap, which makes them easy to polarize. Furthermore, the acquired infrared spectra were compared with the expected harmonic vibrations of the substances 9a–h. On the other hand, binding energy analyses of compounds 9a–h with human corona virus nucleocapsid protein Nl63 (PDB ID: 5epw) were predicted using molecular docking and virtual screening tools. The results showed a promising binding and how these potent compounds were inhibiting the COVID-19 virus. Compound 9h was the most active anti-COVID-19 agent among all the synthesized benzothiazolyl-coumarin derivatives, as it forms five bonds. The presence of the two bromine atoms in its structure was responsible for the potent activity.
中文翻译：
分子对接研究支持的新型荧光苯并噻唑基-香豆素杂化物作为抗 SARS-COVID-2 药物：设计、合成、X 射线晶体结构、DFT 和 TD-DFT/PCM 计算
本研究揭示了新型 3-(benzo[ d ]thiazol-2-yl)-2 H -chromen-2-one 衍生物9a–h的设计和制备。化合物9a和9d的光谱数据和 X 射线晶体学阐明了合成产物的结构。对制备的新化合物进行了荧光测量，良好的结果表明，从未取代的化合物9a到高取代的衍生物9h，增加吸电子基团会降低发光效率（2 Br 重原子）。另一方面，利用B3LYP/6-311G**理论水平对所研究的新型化合物9a-h的几何特性和能量进行量子力学计算优化。使用 TD-DFT/PCM B3LYP 方法研究电子跃迁，该方法使用时间相关的密度泛函计算。此外，该化合物表现出非线性光学特性（NLO）和小的 HOMO-LUMO 能隙，这使得它们易于极化。此外，将获得的红外光谱与物质9a–h的预期谐波进行了比较。另一方面，化合物9a–h的结合能分析使用分子对接和虚拟筛选工具预测了人冠状病毒核衣壳蛋白 Nl63 (PDB ID: 5epw)。结果显示出有希望的结合以及这些有效化合物如何抑制 COVID-19 病毒。化合物9h是所有合成的苯并噻唑基-香豆素衍生物中最活跃的抗 COVID-19 剂，因为它形成五个键。其结构中两个溴原子的存在是产生强效活性的原因。
更新日期：2023-05-23
中文翻译：
分子对接研究支持的新型荧光苯并噻唑基-香豆素杂化物作为抗 SARS-COVID-2 药物：设计、合成、X 射线晶体结构、DFT 和 TD-DFT/PCM 计算
本研究揭示了新型 3-(benzo[ d ]thiazol-2-yl)-2 H -chromen-2-one 衍生物9a–h的设计和制备。化合物9a和9d的光谱数据和 X 射线晶体学阐明了合成产物的结构。对制备的新化合物进行了荧光测量，良好的结果表明，从未取代的化合物9a到高取代的衍生物9h，增加吸电子基团会降低发光效率（2 Br 重原子）。另一方面，利用B3LYP/6-311G**理论水平对所研究的新型化合物9a-h的几何特性和能量进行量子力学计算优化。使用 TD-DFT/PCM B3LYP 方法研究电子跃迁，该方法使用时间相关的密度泛函计算。此外，该化合物表现出非线性光学特性（NLO）和小的 HOMO-LUMO 能隙，这使得它们易于极化。此外，将获得的红外光谱与物质9a–h的预期谐波进行了比较。另一方面，化合物9a–h的结合能分析使用分子对接和虚拟筛选工具预测了人冠状病毒核衣壳蛋白 Nl63 (PDB ID: 5epw)。结果显示出有希望的结合以及这些有效化合物如何抑制 COVID-19 病毒。化合物9h是所有合成的苯并噻唑基-香豆素衍生物中最活跃的抗 COVID-19 剂，因为它形成五个键。其结构中两个溴原子的存在是产生强效活性的原因。
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