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Synthesis, characterizations, and computational studies of new tetrasubstituted imidazole containing a benzothiazole moiety

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Abstract

Tetrasubstituted imidazoles containing a benzothiazole moiety can be formed by a one-pot three-component synthesis from aldehydes, benzil, and 1,3-benzothiazol-2-amine. The synthesized compounds (1–4) are characterized by Fourier-transform infrared spectroscopy (FT-IR), nuclear magnetic resonance spectroscopy (13C, 1H NMR), and mass spectra. The derivatives (1–4) were predicted as anti-breast cancer by docking and DFT study utilization. Discovery Studio Visualizer (DSV) and MGL (Molecular Graphic Laboratory) performed the Autodock procedure. Molecules’ adsorption sites were revealed by measuring the total electron density (TED). Furthermore, variables were utilized to determine which of the molecules were more efficient than the others. The binding energy (Eb) of organic compounds was employed in docking simulations to investigate the inhibitory ability. DFT and docking revealed that 1, 2, and 3 were the most effective inhibitory positions.

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Abbreviations

S:

Chemical softness

χ:

Electronegativity

µ:

Dipole moment

DFT:

Density functional theory

GW 09:

Gaussian 09

HOMO:

Highest occupied molecular orbital

LUMO:

Lowest unoccupied molecular orbital

IP:

Ionization potential

EA:

Electron affinity

MGL:

Molecular Graphic Laboratory

ADT:

Autodock tools

DSV:

Discovery Studio Visualizer

TED:

Total electron density

PDB:

Protein Data Bank

SER:

Serine

ASN:

Asparagine

ARG:

Arginine

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Acknowledgements

We gratefully acknowledge the support of this work by the Chemistry Department, College of Science, Wasit University.

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Authors and Affiliations

  1. Department of Chemistry, College of Science, Wasit University, Wasit, 52002, Iraq

    Kamal Rashid Al-Jorani, Ammar Ferman Abbood, Atheer Abdulsahib Ali & Salam Dawood Hamdan

  2. Medical Laboratory Techniques Department, Al-Farahidi University, Baghdad, Iraq

    Mustafa M. Kadhim

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  1. Kamal Rashid Al-Jorani
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  2. Ammar Ferman Abbood
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  3. Atheer Abdulsahib Ali
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  4. Mustafa M. Kadhim
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Contributions

KRA-J: experimental part. AFA: write and edit. AAA: write and edit. MMK: supervisor and software. SDH: experimental part.

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Correspondence to Kamal Rashid Al-Jorani or Mustafa M. Kadhim.

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Al-Jorani, K.R., Abbood, A.F., Ali, A.A. et al. Synthesis, characterizations, and computational studies of new tetrasubstituted imidazole containing a benzothiazole moiety. Struct Chem 34, 1143–1156 (2023). https://doi.org/10.1007/s11224-022-02069-w

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