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Charge Density Study, DFT Calculations, Hirshfield Surface Analysis and Molecular Docking of (Z)-3-N-(Ethyl)-2-N '-(3-methoxyphenyl imino) thiazolidine-4-one

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Abstract

In this work, the electron density distribution of (Z)-3-N-(ethyl)-2-N '-(3-methoxyphenyl imino) thiazolidine-4-one is determined by single-crystal X-ray refinements using a spherical structure factors and multipolar model of Hansen and Coppens. The following crystal properties are determined: laplacian of electron density and critical points. These parameters are basic for understanding the nature of intra- and intermolecular charge transfer and to highlight the chemical reactivity of the molecule. From the deformation density maps, density accumulations are visible in bonding as well as in the lone-pair regions of oxygen atoms (O1 and O2). The results of reduced density gradient, of natural bond orbital and of Hirshfeld surface analysis allow obtaining respectively; information’s of the intra non-bonded interactions, charge transfer and to understand what kind of interatomic contacts give the largest contributions in crystal structure. The relative high value of local reactivity descriptors indicate that S atom is the most preferred site for nucleophilic attacks whereas C4 and C8 sites are the most nucleophilic centers. In addition, the compound under investigation presents a biological activity when it is docked into the protein (PDB ID: 2AZ5) with the binding energy system of –6.3 kcal/mol. This compound showed excellent interaction with amino acids constitutes this protein and showed significant inhibition of tumor necrosis factor.

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Authors and Affiliations

  1. Chemistry Department, Faculty of Exact Sciences and Informatic, Hassiba Benbouali University, 02000, Chlef, Algeria

    Youcef Megrouss, Nourdine Boukabcha, Mansour Azayez & Souad Bennabi

  2. Laboratory of Technology and Solid Properties (LTPS), Abdelhamid Ibn Badis University of Mostaganem, BP 227, 27000, Mostaganem, Algeria

    Youcef Megrouss, Salem Yahiaoui, Nourdine Boukabcha, Asma Nekrouf, Merzouk Saidj, Abdelkader Chouaih & Mokhtaria Drissi

  3. Higher Normal School, 27000, Mostaganem, Algeria

    Salem Yahiaoui

  4. Department of Material Science, Faculty of Science and Technology, Tissemsilt University, Tissemsilt, Algeria

    Sid Ahmed Kaas

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  1. Youcef Megrouss
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Megrouss, Y., Yahiaoui, S., Boukabcha, N. et al. Charge Density Study, DFT Calculations, Hirshfield Surface Analysis and Molecular Docking of (Z)-3-N-(Ethyl)-2-N '-(3-methoxyphenyl imino) thiazolidine-4-one. Russ. J. Phys. Chem. 97, 1731–1745 (2023). https://doi.org/10.1134/S0036024423080319

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