Spectroscopic and theoretical investigation of the potential anti-tumor and anti-microbial agent, 3-(1-((2-hydroxyphenyl)amino)ethylidene)chroman-2,4-dione

The coumarin–orthoaminophenol derivative was prepared under mild conditions. Based on crystallographic structure, IR and Raman, 1H and 13C NMR spectra the most applicable theoretical method was determined to be B3LYP-D3BJ. The stability and reactivity parameters were calculated, in the framework of...

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Bibliographic Details
Published in:Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy Molecular and biomolecular spectroscopy, 2019-01, Vol.206, p.421-429
Main Authors: Avdović, Edina H., Dimić, Dušan S., Dimitrić Marković, Jamina M., Vuković, Nenad, Radulović, Milanka Đ., Živanović, Marko N., Filipović, Nenad D., Đorović, Jelena R., Trifunović, Srećko R., Marković, Zoran S.
Format: Article
Language:English
Subjects:
Antimicrobial activity
Cell cytotoxicity
Coumarin
FTIR
Molecular docking
NMR
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Summary:The coumarin–orthoaminophenol derivative was prepared under mild conditions. Based on crystallographic structure, IR and Raman, 1H and 13C NMR spectra the most applicable theoretical method was determined to be B3LYP-D3BJ. The stability and reactivity parameters were calculated, in the framework of NBO, QTAIM and Fukui functions, form the optimized structure. This reactivity was then probed in biological systems. The antimicrobial activity towards four bacteria and three fungi species was examined and activity was proven. In vitro cytotoxic effects, against human epithelial colorectal carcinoma HCT-116 and human healthy lung MRC-5 cell lines, of the investigated substance are also tested. Compound showed significant cytotoxic effects on HCT-116 cells, while on MRC-5 cells showed no cytotoxic effects. The effect of hydroxy group in ortho-position on the overall reactivity of molecule was examined through molecular docking with Glutathione-S-transferases. [Display omitted] •The cumarine derivative with o-aminophenol was synthesized under mild conditions.•The structure and spectroscopic properties of compound 3 are confirmed by DFT.•The MIC and IZ values of 3 are comparable to the commercially active drugs•Investigated substance revealed surprising effect on cancer cells HCT-116.•Possible interactions between 3 and Glutathione-S-transferase were revealed by MD.
ISSN:1386-1425
DOI:10.1016/j.saa.2018.08.034