“…Nevertheless, in present conditions, the reaction leads to formation in 95% yield of the isomer shown in Figure 2. The same observation was noted for our other keto-enol derivatives recently postponed [21][22][23][24][25]. …”
Abstract:Molecules bearing β-keto-enol functionality are potential candidates for coordination chemistry. Reported herein is the first synthesis and use of a novel designed ligand based on β-keto-enol group embedded with pyridine and thiophene moieties. The product was prepared in a one-step procedure by mixed Claisen condensation and was characterized by EA, m/z, FT-IR, ( 1 H, 13 C) NMR and single-crystal X-ray diffraction analysis. The new structure was grafted onto silica particles to afford a chelating matrix which was well-characterized by EA, FT-IR, solid-state 13 C-NMR, BET, BJH, SEM and TGA. The newly prepared organic-inorganic material was used as an adsorbent for efficient solid-phase extraction (SPE) of Cu(II), Zn(II), Cd(II) and Pb(II) from aqueous solutions and showed a capture capacity of 104.12 mg¨g´1, 98.90 mg¨g´1, 72.02 mg¨g´1, and 65.54 mg¨g´1, respectively. The adsorption capacity was investigated, in a batch method, using time of contact, pH, initial concentration, kinetics (Langmuir and Freundlich models), and thermodynamic parameters (∆G˝, ∆H˝and ∆S˝) of the system effects.
“…Nevertheless, in present conditions, the reaction leads to formation in 95% yield of the isomer shown in Figure 2. The same observation was noted for our other keto-enol derivatives recently postponed [21][22][23][24][25]. …”
Abstract:Molecules bearing β-keto-enol functionality are potential candidates for coordination chemistry. Reported herein is the first synthesis and use of a novel designed ligand based on β-keto-enol group embedded with pyridine and thiophene moieties. The product was prepared in a one-step procedure by mixed Claisen condensation and was characterized by EA, m/z, FT-IR, ( 1 H, 13 C) NMR and single-crystal X-ray diffraction analysis. The new structure was grafted onto silica particles to afford a chelating matrix which was well-characterized by EA, FT-IR, solid-state 13 C-NMR, BET, BJH, SEM and TGA. The newly prepared organic-inorganic material was used as an adsorbent for efficient solid-phase extraction (SPE) of Cu(II), Zn(II), Cd(II) and Pb(II) from aqueous solutions and showed a capture capacity of 104.12 mg¨g´1, 98.90 mg¨g´1, 72.02 mg¨g´1, and 65.54 mg¨g´1, respectively. The adsorption capacity was investigated, in a batch method, using time of contact, pH, initial concentration, kinetics (Langmuir and Freundlich models), and thermodynamic parameters (∆G˝, ∆H˝and ∆S˝) of the system effects.
“…The two independent molecular units are almost coplanar, as shown by the angle of only 1.96(3)° measured between their mean planes (calculated with all the non-H atoms). The bonds lengths and angles measured in the two molecules are very close and in range of values found in the literature for similar compounds [34–38]. Fig.…”
BackgroundNowadays, is emerging a new generation of highly promising inhibitors bearing the β-ketoenol functionality. The present work relates to the first synthesis, the structure determination, the DFT studies and the use of a new biomolecule designed with a β-ketoenol group bounded to a pyrazolic moiety.ResultA novel β-ketoenol-pyrazole has been synthesized, well characterized and its structure was confirmed by single crystal X-ray diffraction. The electron densities and the HOMO–LUMO gap have been calculated using the DFT method with BLYP, PW91, PWC functionals and 6-31G* basis set. An evaluation of the molecule stability is provided by a NBO analysis and the calculated Fukui and Parr functions have been used to locate the reactive electrophile and nucleophile centers in the molecule. The synthesized compound, screened for its in vitro antifungal behavior against the Fusarium oxysporum f.sp. albedinis FAO fungal strains, shows a moderate activity with an inhibition percentage of 46%. The product was also tested against three bacterial strains (Escherichia coli, Bacillus subtilis and Micrococcus luteus), but no significant effect was observed against these organisms.ConclusionsDensity functional calculations are used to evaluate the HOMO–LUMO energy gap, the molecular electrostatic potential and to provide a natural bond orbital analysis. The measured antimicrobial activities encourage us to continue searching for other structures, likely to be good antifungal candidates.Electronic supplementary materialThe online version of this article (10.1186/s13065-018-0492-4) contains supplementary material, which is available to authorized users.
“…The method has experienced rapid growth and many improvements over the last two decades and the number of publications associated with molecular docking studies has increased enormously. 21 In continuation of our recent works in the field of the synthesis of novel -keto-enol heterocyclic derivatives through efficient and simple routes and of the study of their biological activities, 17,[22][23][24][25][26][27][28][29][30][31] we report in the present investigation on the synthesis and the properties of a novel series of pyrazoles with the -keto-enol functionality as powerful moieties especially in fungal activity. To the best of our knowledge, this is the first real study aiming to develop diversified structures of keto-enol pyrazoles.…”
Section: Introductionmentioning
confidence: 94%
“…Accordingly, our previously prepared products were exclusively obtained in the -keto-enol tautomer form, governed by the resonance driving force, as confirmed by XRD. [22][23][24][25][26][27] Herein, as proved by its crystal structure determined from the X-ray diffraction study, compound 10 was also found to exist with the -keto-enol tautomer form.…”
Section: Compounds Chemistrymentioning
confidence: 99%
“…The bonds lengths and angles in the molecule are comparable to those found in previous works for other similar compounds. [22][23][24][25][26][27]46 Molecular packing in the monoclinic lattice is such that molecules superimpose along the a and b axes as shown by the projections given in Figure 3 against one fungal strain (Fusarium oxysporum f.sp albedinis) by the agar diffusion method. Surprisingly, the antimicrobial assay revealed that all the screened compounds possessed very weak or no antibacterial effect against all used strains.…”
Section: Journal Of Chemical Information and Modelingmentioning
A new family of promising inhibitors bearing -keto-enol functionality with greatly improved pharmacophore properties has prepared. Herein, a series of novel derivatives of -keto-enol group embedded with pyrazolic moiety has been designed and synthesized via a one-step procedure using mixed Claisen condensation in the attempt to develop potential antifungal agents. The structures of the synthesized compounds were confirmed by elemental analysis, FT-IR, ESI/LC-MS, 1 H and 13 C NMR. In addition, X-ray diffraction analysis (XRD) was used to determine the single crystal structure of compound 10. All the newly compounds have been evaluated for their in vitro antifungal and antibacterial activities. Interestingly, the results indicate that most of the compounds display notable antifungal activity close to that of the benomyl fungicide taken as the standard drug. For the most active compound and for benomyl, a correlation has been evidenced between the experimental antifungal activity and the theoretical predictions by DFT calculations and molecular docking against Fgb1 protein.
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