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Thio/carbohydrazone derivatives from iso(thio)/cyanates: preparation, structure elucidation, DFT studies, antimicrobial activity and DNA interactions

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Abstract

New thio/carbohydrazone derivatives (1–10) have been synthesized from various iso(thio)/cyanates. The chemical structures of synthesized compounds were elucidated with UV–Vis, IR, 1H NMR, 13C NMR spectroscopic methods, and elemental analysis. Antimicrobial activities of all synthesized compounds against Gram-positive, Gram-negative mold and yeast were screened by disc diffusion and microdilution methods. Ground state structures were obtained with the DFT approach, and also, experimental data were supported by spectroscopy calculations. In addition to calculating the reactivity parameters, intramolecular interactions and electron density distributions were analyzed and approaches to the antimicrobial properties of the compounds were presented. Furthermore, the interaction between the compounds and pBR322 plasmid DNA was investigated by gel electrophoresis. In this study to investigate the antibacterial and antifungal activity of new thio/carbohydrazone derivatives (1–10), it was determined that compound 7 has a remarkable inhibitory effect on S. aureus (12.66 ± 1.52 mm) and compound 10 on S. aureus (20.33 ± 0.57 mm), S. mutans (16.33 ± 0.57 mm) and A. niger (15.33 ± 0.57 mm). The interaction results of compounds 1–10 with plasmid pBR322 DNA showed that compounds 1, 8, and 10 caused a reduction in the densities of form I and form II DNA. Compounds 2–7, 9 caused a double-stranded break of plasmid DNA (Form III).

Graphical abstract

New thio/carbohydrazone derivatives have been synthesized. Structures of all compounds have been elucidated with spectroscopic approaches. Antimicrobial activities of all synthesized compounds were determined. The interaction between the compounds and pBR322 plasmid DNA was investigated by gel electrophoresis. DFT studies were performed about reactivity parameters, intramolecular interactions and electron density distributions.

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Acknowledgements

The DFT calculations reported in this paper were partially performed at TUBITAK ULAKBIM, High Performance and Grid Computing Center (TRUBA resources). We would like to thank Dr. Seyhan Ozturk at Ondokuz Mayıs University for taking the UV-Vis spectra.

Funding

This research did not receive any specific grant from funding agencies in the public, commercial, or not-for-profit sectors.

Author information

Authors and Affiliations

  1. Department of Biomedical Engineering, Kastamonu University, Kastamonu, Turkey

    Muhammet Serdar Çavuş

  2. Department of Chemistry Education, Ondokuz Mayis University, Samsun, Turkey

    Hasan Yakan

  3. Şerefeddin Sabuncuoğlu Health Services Vocational School, Amasya University, Amasya, Turkey

    Ceren Başkan

  4. Department of Food Engineering, Kafkas University, Kars, Turkey, 36100

    Musa Erdoğan

  5. Department of Chemistry, Kastamonu University, Kastamonu, Turkey

    Halit Muğlu

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  1. Muhammet Serdar Çavuş
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  4. Musa Erdoğan
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  5. Halit Muğlu
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Contributions

MSÇ: Theoretical Calculations, Writing–Review. HY: Spectroscopic Characterization, Writing–Review, Visualization & Editing. CB: Biological studies, Writing–Review. ME: Spectroscopic Characterization, Writing–Review. HM: Synthesis, Characterization, Writing–Review. All authors reviewed the manuscript.

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Correspondence to Hasan Yakan or Ceren Başkan.

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Çavuş, M., Yakan, H., Başkan, C. et al. Thio/carbohydrazone derivatives from iso(thio)/cyanates: preparation, structure elucidation, DFT studies, antimicrobial activity and DNA interactions. Res Chem Intermed 49, 2639–2667 (2023). https://doi.org/10.1007/s11164-023-05014-6

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