Journal
RESEARCH ON CHEMICAL INTERMEDIATES
Volume 49, Issue 6, Pages 2639-2667Publisher
SPRINGER
DOI: 10.1007/s11164-023-05014-6
Keywords
Thio/carbohydrazones; Spectroscopic studies; DFT; Antimicrobial activity; DNA interactions
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New thio/carbohydrazone derivatives (1-10) were synthesized and their chemical structures were determined by UV-Vis, IR, H-1 NMR, C-13 NMR spectroscopy, and elemental analysis. The antimicrobial activities of the compounds were evaluated against Gram-positive, Gram-negative, and yeast using disc diffusion and microdilution methods. The study also investigated the interaction between the compounds and plasmid DNA.
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, H-1 NMR, C-13 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 p(BR322) 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).
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