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Title: Synthesis, properties and antimycobacterial activity of 5-arylidene derivatives of imidazol-4-one


The large series of 5-arylidene-2-arylalkylthio/amine/hydrazide/isoniazid derivatives of imidazol-4-one was synthesized and examined in vitro against M tuberculosis. The preparation of the target compounds by the traditional method according to the literature procedures or by means of microwaves was described. The structure and purity of the obtained derivatives were confirmed by elemental and spectral analyses (IR, 1H-NMR) and the thin-layer chromatography. The study on 3-D structure and the tautomeric equilibrium observed among the investigated compounds in the solution and in the solid state were performed by means of: • 1H-NMR, 13C-NMR, 15N-NMR spectra analyses • X-ray crystallography • molecular modelling methods - conformational analysis and calculation of rotation barier energy with application of several computer programs Physicochemical (lipophylic) properties of the compounds were determined by the theoretical and experimental way with application of the reversed phase thin layer chromatography method. In order to determine the durability of new derivatives in the DMF and DMSO solutions, in acidic and basic pH, the suitable tests were performed. All the compounds were tested on their antimycobacterial activity against M tuberculosis H37Rv according to TAACF (Tuberculosis Antimicrobial Acquisition and Coordinating Facility) screening program. The most effective com ; pounds - 3-chloro-, 3-tluoro, 2-fluoro-, 4-fluorobenzylidene- 2-izoniazid derivatives with MIC in vitro ≤ 3.13 μg/ml were successfully tested in the cytotoxity, macrophage activity, single drug resistant MIC and MBC assays and were classified to the in vivo assay. The study on computer metabolism simulation of investigated compounds and the structure-antimycobacterial activity analysis was performed as well.

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2 - studia doktoranckie

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Wydział Farmaceutyczny


Kieć-Kononowicz, Katarzyna

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tylko w bibliotece

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Last modified:

Jul 18, 2022

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Nov 21, 2012

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ZB-100461 Jul 18, 2022


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