DFT/TD-DFT calculations, spectroscopic characterizations (FTIR, NMR, UV-vis), molecular docking and enzyme inhibition study of 7-benzoyloxycoumarin
DFT/TD-DFT calculations, spectroscopic characterizations (FTIR, NMR, UV-vis), molecular docking and enzyme inhibition study of 7-benzoyloxycoumarin
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DOI：
10.1016/j.compbiolchem.2018.01.007
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发表时间：
2018-04-01
影响因子：
3.1
通讯作者：
Ahmad, Shabbir
中科院分区：
文献类型：
--
作者：
Alam, Mahboob;Alam, Mohammad Jane;Ahmad, Shabbir
本文报道了具有药理活性的7-苯甲酰氧基香豆素(2)分子的量子化学研究、光谱表征和生物活性。利用势能表面（PES）扫描来寻找该化合物最稳定的分子几何结构。理论得到了该化合物基态稳定几何结构、红外、紫外-可见吸收光谱和核磁共振（C-13, H-1）光谱，并与实验结果进行了比较。给出了各种理论分子参数，如分子能量、原子电荷、偶极矩、热力学参数、供体-受体自然键轨道（NBO）超共轭相互作用能、前沿分子轨道能、HOMO-LUMO间隙、分子静电势、化学反应性描述符、分子极化率和非线性光学（NLO）性质。此外，还研究了三维Hirshfeld曲面和相关的二维指纹图谱。研究了各种非共价相互作用的百分比，并通过赫什菲尔德表面指纹图谱进行了图示。与对照药物加兰他明相比，7-苯甲酰氧基香豆素对丁基胆碱酯酶（BuChE）具有良好的抑制活性。通过分子对接，将化合物引入丁基胆碱酯酶活性位点的x射线晶体结构中，寻找可能的结合模式。分子对接结果表明，香豆素7-苯甲酰氧基衍生物可能具有酶抑制剂活性。(c) 2018 Elsevier Ltd.版权所有。
The quantum chemical study, spectroscopic characterization and biological activity of the pharmaceutically active 7-benzoyloxycoumarin (2) molecule have been presented. Potential energy surface (PES) scanning has been performed to search for the most stable molecular geometry of the present compound. The stable geometry in the ground state, IR, UV-Vis absorption and NMR (C-13, H-1) spectra of the title compound were theoretically obtained and compared with the experimental one. Various theoretical molecular parameters like molecular energy, atomic charges, dipole moment, thermodynamic parameters, donor-acceptor natural bond orbital (NBO) hyperconjugative interaction energies, frontier molecular orbitals energies, HOMO-LUMO gap, molecular electrostatic potential, chemical reactivity descriptors, molecular polarizability and non-linear optical (NLO) properties are presented. Moreover, the 3D Hirshfeld surfaces and the associated 2D fingerprint plots have been explored. The percentages of various non-covalent interactions are studied and pictorialized by fingerprint plots of Hirshfeld surface. 7-Benzoyloxycoumarin has shown promising inhibitory activity against butrylcholinesterase (BuChE) as compared to the reference drug, galantamine. Molecular docking is carried to introduce compound into the X-ray crystal structures of butrylcholinesterase at the active site to find out the probable binding mode. The results of molecular docking indicated that 7-benzoyloxy derivative of coumarin may show enzyme inhibitor activity. (c) 2018 Elsevier Ltd. All rights reserved.