Synthesis, crystal structure, hirshfeld surface analysis, spectroscopic, biological and first-principles studies of novel aminocoumarins

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dc.authoridSERDAROGLU, Goncagul/0000-0001-7649-9168
dc.authoridBEN HASSEN, Rached/0000-0003-3616-8385
dc.authoridDusek, Michal/0000-0001-9797-2559
dc.authoridMarzouki, Riadh/0000-0002-2502-2164
dc.authoridBRAHMIA, Ameni/0000-0001-7434-6563
dc.authoridEigner, Vaclav/0000-0003-1014-3980
dc.contributor.authorBejaoui, Linda
dc.contributor.authorBrahmia, Ameni
dc.contributor.authorMarzouki, Riadh
dc.contributor.authorDusek, Michal
dc.contributor.authorEigner, Vaclav
dc.contributor.authorSerdaroglu, Goncagul
dc.contributor.authorKaya, Savas
dc.date.accessioned2024-10-26T18:11:22Z
dc.date.available2024-10-26T18:11:22Z
dc.date.issued2020
dc.departmentSivas Cumhuriyet Üniversitesi
dc.description.abstractTwo novel aminocoumarins 3-(1-(2 aminophenylamino) ethylidene)chromene-2,4-dione, noted (1) and 3-(1-(2-1-(2, 4-dioxochromene-3-ylidene) ethylamino)phenylamino) ethylidene) chromene-2,4-dione,noted (2), were synthesized from 3-acetyl-4-hydroxycoumarin and ortho-phenylenediamine in absolute ethanol and characterized by spectroscopies methods (FT-IR, UV-vis and fluorescence). The crystal structures of the mentioned compounds were solved from single-crystal diffraction data at low temperature. The compound (1) crystallizes in the orthorhombic system with space group Iba2 while (2) is monoclinic with space group P(2)1/c . Hirshfeld surface analysis indicates the presence of the pi-pi stacking in the aminocoumarin structures with the contribution of 7.8% for (1) and 8.7% for (2) of the total Hirshfeld area. The optimized DFT geometries (B3PW91/6-311 G (2df, p)) and the spectral simulations agree well with the experimental data. Theoretical reactivity behavior was assessed, taking into account HOMOLUMO diagrams and Molecular Electrostatic Potential maps. The two aminocoumarins derivatives have fluorescence properties. Analysis of the photoluminescence spectra shows that the emission intensity is high for the solutions of the two compounds in polar aprotic solvents (DMSO, DMF). The aminocoumarins were monitored for antimicrobial activity using the disk diffusion method. The coumarin (1) is effective against S. aureus (gram-positive bacteria) and S. typhy (gram-negative bacteria), but the coumarin (2) showed markedly weak antibacterial activity. (C) 2020 Elsevier B.V. All rights reserved.
dc.description.sponsorshipDeanship of Scientific Research at King Khalid University [R.G.P.1/141/40]; Czech Science Foundation [18-10504S, CZ.2.16/3.1.00/24,510]
dc.description.sponsorshipThis research was funded by the Deanship of Scientific Research at King Khalid University, grant number R.G.P.1/141/40. The crystallographic part was supported by the project 18-10504S of the Czech Science Foundation using instruments of the ASTRA laboratory established within the Operation program Prague Competitiveness -project CZ.2.16/3.1.00/24,510.
dc.identifier.doi10.1016/j.molstruc.2020.128862
dc.identifier.issn0022-2860
dc.identifier.issn1872-8014
dc.identifier.scopus2-s2.0-85088013443
dc.identifier.scopusqualityQ2
dc.identifier.urihttps://doi.org/10.1016/j.molstruc.2020.128862
dc.identifier.urihttps://hdl.handle.net/20.500.12418/30648
dc.identifier.volume1221
dc.identifier.wosWOS:000598076400013
dc.identifier.wosqualityQ3
dc.indekslendigikaynakWeb of Science
dc.indekslendigikaynakScopus
dc.language.isoen
dc.publisherElsevier
dc.relation.ispartofJournal of Molecular Structure
dc.relation.publicationcategoryMakale - Uluslararası Hakemli Dergi - Kurum Öğretim Elemanı
dc.rightsinfo:eu-repo/semantics/closedAccess
dc.subjectAminocoumarin derivatives
dc.subjectFluorescence
dc.subjectHirshfeld surfaces
dc.subjectDFT
dc.subjectAntimicrobial activity
dc.titleSynthesis, crystal structure, hirshfeld surface analysis, spectroscopic, biological and first-principles studies of novel aminocoumarins
dc.typeArticle

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