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Theoretical and experimental approaches of new Schiff bases: efficient synthesis, X-ray structures, DFT, molecular modeling and ADMET studies

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Abstract

Two new Schiff bases (E)-1-(3-((2-hydroxy-3-methylbenzylidene)amino)phenyl)ethan-1-one (1) and (E)-2-(((3-chloro-4-(4-chlorophenoxy)phenyl)imino)methyl)-6-methylphenol (2) were synthesized by already reported method on reflux. Characterization of targeted compounds was performed by spectroscopic techniques and X-ray diffraction analysis. Single-crystal X-ray diffraction studies showed that compound 1 is orthorhombic, while 2 is triclinic. In the crystalline molecules, intermolecular interactions have been observed by using the Hirshfeld surface analysis along 2D interactions. Molecular Operating Environment software was used for the docking studies which administer the potential appliance of the targeted compounds against AChE and BChE. Results of the docking study depicted that compound 1 is less active than that of compound 2 across both enzymes. To perform the optimization of the Schiff base, 6-31G(d,p) basis set and B3LYP method were used. DFT calculations were used to measure the associated energies of the orbitals and also correlate the bond angle and bong length of the synthesized compounds with the experimental values. It was seen from results that experimental and DFT calculation are in close agreement. In order to check the therapeutic properties, in silico ADMET model was adopted which revealed that the different properties of the synthesized molecules are drug-like.

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Authors and Affiliations

  1. Department of Physics, Faculty of Arts and Sciences, Ondokuz Mayıs University, Samsun, Turkey

    Necmi Dege

  2. Department of Chemistry, University of Gujrat, Hafiz Hayat Campus, Gujrat, Pakistan

    Muhammad Asam Raza & Muhammad Waseem Mumtaz

  3. Department of Chemistry, Faculty of Arts and Sciences, Ondokuz Mayıs University, Samsun, Turkey

    Onur Erman Doğan

  4. Department of Chemical Engineering, Yeditepe University, 34755, İstanbul, Turkey

    Tuğgan Ağar

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  1. Necmi Dege
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  2. Muhammad Asam Raza
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  4. Tuğgan Ağar
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  5. Muhammad Waseem Mumtaz
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Correspondence to Muhammad Asam Raza.

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Dege, N., Raza, M.A., Doğan, O.E. et al. Theoretical and experimental approaches of new Schiff bases: efficient synthesis, X-ray structures, DFT, molecular modeling and ADMET studies. J IRAN CHEM SOC 18, 2345–2368 (2021). https://doi.org/10.1007/s13738-021-02194-z

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