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Organohalogen chalcones: design, synthesis, ADMET prediction, molecular dynamics study and inhibition effect on acetylcholinesterase and carbonic anhydrase

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Abstract

In an effort to discover potential acetylcholinesterase (AChE) and carbonic anhydrase (CA) inhibitors, a novel series of organohalogen chalcone derivatives (12–20, 23–30) was synthesized, and their chemical structures were characterized by spectral analysis. They showed a highly potent inhibition effect on AChE and hCAs (Ki values range from 5.07 ± 0.062 to 65.53 ± 4.36 nM for AChE, 13.54 ± 2.55 to 94.11 ± 10.39 nM for hCA I, and 5.21 ± 0.54 to 57.44 ± 3.12 nM for hCA II). In addition, the chalcone derivatives with the highest inhibitor score docked into the active site of the indicated metabolic enzyme receptors, and their absorption, metabolism, and toxic properties were evaluated according to ADMET's estimation.Compounds 16 and 19 exhibited the highest inhibition score, emerged as lead compounds, and inspired the development of more potent compounds.

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Authors and Affiliations

  1. Department of Chemistry, Faculty of Science, Ataturk University, 25240, Erzurum, Turkey

    Busra Ozturk Aydin & Derya Aktas Anil

  2. Department of Chemistry and Chemical Process Technologies, Technical Sciences Vocational School, Ataturk University, 25240, Erzurum, Turkey

    Derya Aktas Anil

  3. Department of Pharmacy Services, Nihat Delibalta Göle Vocational School, Ardahan University, 75002, Ardahan, Turkey

    Yeliz Demir

  4. Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Inonu University, Malatya, Turkey

    Mehmet Abdullah Alagoz

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  1. Busra Ozturk Aydin
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  3. Yeliz Demir
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  4. Mehmet Abdullah Alagoz
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Contributions

Busra Ozturk Aydın synthesized all the molecules in the manuscript. Yeliz Demir carried out enzyme inhibition studies. Mehmet Abdullah Alagöz carried out computer biology studies. Derya Aktas Anıl made the characterization of all molecules.

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Correspondence to Derya Aktas Anil.

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Aydin, B.O., Anil, D.A., Demir, Y. et al. Organohalogen chalcones: design, synthesis, ADMET prediction, molecular dynamics study and inhibition effect on acetylcholinesterase and carbonic anhydrase. Mol Divers (2024). https://doi.org/10.1007/s11030-023-10774-9

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  • DOI: https://doi.org/10.1007/s11030-023-10774-9

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