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Synthesis, Antibacterial, Antioxidant and DFT Computational Studies of Acetophenone-Based Chalcone Derivatives

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Abstract

Six B-ring substituted chalcone derivatives were synthesized by aldol condensation reactions of acetophenone with ortho-, meta- and para-hydroxy and their corresponding nitro group-functionalized benzaldehydes. These were used to study their spectral, anti-bacterial and anti-oxidant properties. The FT-IR and 1H and 13C-NMR spectra of these derivatives, as well as in some cases from the literature, were used to confirm their structural information. A density functional theory (DFT) computational study was undertaken to investigate the changes resulting from the replacement of the electron-donating hydroxyl groups with the corresponding electron-withdrawing nitro groups and with consideration of all of their possible E/Z and s-cis/s-trans geometrical and regioisomers. The DFT computational data show that in all cases except for the B-ring ortho-nitro-substituted derivatives 5a and its regioisomer 5a′, the s-cis-(E) isomers, are thermodynamically more stable than those of the corresponding s-cis-(Z)– and s-trans-(E/Z) isomers. Furthermore, time-dependent-DFT calculations were conducted to generate vertical excitation energies, absorption wavelengths and the oscillator strengths of the chalcone derivatives. The HOMO–LUMO results and some other physicochemical parameters of the derivatives are compared with their chemical reactivities.

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Synthesis, antibacterial, antioxidant and DFT computational studies of acetophenone-based chalcone derivatives

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Data Availability Statement

The data that support the findings of this study are available in the supplementary material of this article.

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Acknowledgments

This work was supported by Bangladesh Council of Scientific and Industrial Research (BCSIR) and partly funded (Project no. SRG-226626) by Ministry of Science and Technology (MOST, BD), Bangladesh. Dr. Md. Wahidul Islam and Rabeya Akter are thankful to BCSIR for Postdoctoral and Prof. Nurul Afsar Khan Postgraduate Fellowship. The authors extend their appreciation to Bank Aljazira for funding this project and also acknowledge King Abdullah Institute for Nanotechnology at King Saud University for supporting this initiative.

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Authors and Affiliations

  1. Synthesis Laboratory, Chemical Research Division, Bangladesh Council of Scientific and Industrial Research (BCSIR), Dhanmondi, Dhaka, 1205, Bangladesh

    Md. Wahidul Islam, Rabeya Akter, Md. Monarul Islam, Rashedul Islam, Fatema Tuz Zohora, Tayebur Rahman Limon & Md. Aftab Ali Shaikh

  2. Institute of National Analytical Research and Service (INARS), Bangladesh Council of Scientific and Industrial Research (BCSIR), Dhanmondi, Dhaka, 1205, Bangladesh

    A. H. M. Shofiul Islam Molla Jamal

  3. Industrial Microbiology Section, Institute of Food Science and Technology (IFST), Bangladesh Council of Scientific and Industrial Research (BCSIR), Dhanmondi, Dhaka, 1205, Bangladesh

    Abhijit Chowdhury

  4. Biological and Environmental Sensing Research Unit, King Abdullah Institute for Nanotechnology, King Saud University, 11451, Riyadh, Saudi Arabia

    Shofiur Rahman & Abdullah Alodhayb

  5. Department of Physics and Astronomy, College of Science, King Saud University, 11451, Riyadh, Saudi Arabia

    Abdullah Alodhayb

  6. Pharmaceutical Sciences Research Division, Bangladesh Council of Scientific and Industrial Research (BCSIR), Dhanmondi, Dhaka, 1205, Bangladesh

    Satyajit Roy Rony

  7. Department of Chemistry, University of Dhaka, Dhaka, 1000, Bangladesh

    Tayebur Rahman Limon, Md. Aftab Ali Shaikh & Ahsan Habib

  8. Department of Chemistry, Memorial University of Newfoundland, St. John’s, NL, A1B 3X7, Canada

    Paris E. Georghiou

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  1. Md. Wahidul Islam
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42250_2024_891_MOESM1_ESM.docx

Supplementary file1. The experimental information, spectroscopic studies (including 1HNMR, IR spectra), and theoretical studies are reported in the supporting information. (DOCX 6087 kb)

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Islam, M.W., Akter, R., Islam, M.M. et al. Synthesis, Antibacterial, Antioxidant and DFT Computational Studies of Acetophenone-Based Chalcone Derivatives. Chemistry Africa 7, 1803–1816 (2024). https://doi.org/10.1007/s42250-024-00891-9

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