Crystal structure of (Z)-1-(1,5-dimethyl-1H-pyrazol-3-yl)-3-hydroxy-3-(p-toly)prop-2-en-1-one, C15H16N2O2

Radi, Smaail; Tighadouini, Saïd; Eddike, Driss; Tillard, Monique; Mabkhot, Yahia N.

doi:10.1515/ncrs-2016-0199

Cited by 4 publications

(10 citation statements)

References 11 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…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]. …”

Section: X-ray Crystal Structure Descriptionsupporting

confidence: 86%

β-Keto-enol Tethered Pyridine and Thiophene: Synthesis, Crystal Structure Determination and Its Organic Immobilization on Silica for Efficient Solid-Liquid Extraction of Heavy Metals

et al. 2016

Self Cite

View full text Add to dashboard Cite

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.

show abstract

Section: X-ray Crystal Structure Descriptionsupporting

confidence: 86%

β-Keto-enol Tethered Pyridine and Thiophene: Synthesis, Crystal Structure Determination and Its Organic Immobilization on Silica for Efficient Solid-Liquid Extraction of Heavy Metals

et al. 2016

Self Cite

View full text Add to dashboard Cite

show abstract

“…In continuation of our recent works in the field of the synthesis of novel β-keto–enol heterocyclic derivatives through efficient and simple routes and of the study of their biological activities, ,− we report in the present investigation on the synthesis and the properties of a novel series of pyrazoles with the β-keto–enol functionality as powerful moieties especially in fungal activity. To the best of our knowledge, this is the first real study aimed at developing diversified structures of keto–enol pyrazoles.…”

Section: Introductionmentioning

confidence: 91%

“…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

confidence: 99%

“…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: 96%

See 2 more Smart Citations

Novel β-keto–enol Pyrazolic Compounds as Potent Antifungal Agents. Design, Synthesis, Crystal Structure, DFT, Homology Modeling, and Docking Studies

Tighadouini

Radi

Abrigach

et al. 2019

J. Chem. Inf. Model.

Self Cite

View full text Add to dashboard Cite

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.

show abstract

Synthesis, Biochemical Characterization, and Theoretical Studies of Novel β-Keto-enol Pyridine and Furan Derivatives as Potent Antifungal Agents

et al. 2020

Self Cite

View full text Add to dashboard Cite

In the present study, we report the design and synthesis of new derivatives of the β-keto-enol grafted on pyridine and furan moieties ( L 1 – L 11 ). Structures of compounds were fully confirmed by Fourier transform infrared spectroscopy (FT-IR), 1 H NMR, 13 C NMR, electrospray ionization/liquid chromatography-mass spectrometry (ESI/LC-MS), and elemental analysis. The compounds were screened for antifungal and antibacterial activities ( Escherichia coli , Bacillus subtilis , and Micrococcus luteus ). In vitro evaluation showed significant fungicidal activity for L 1 , L 4 , and L 5 against fungal strains ( Fusarium oxysporum f.sp albedinis ) compared to the reference standard. Especially, the exceptional activity has been demonstrated for L 1 with IC 50 = 12.83 μg/mL. This compound and the reference benomyl molecule also showed a correlation between experimental antifungal activity and theoretical predictions by Petra/Osiris/Molinspiration (POM) calculations and molecular coupling against the Fgb1 protein. The highest inhibition of bacterial growth for L 1 is due to its strongest binding to the target protein. This report may stimulate the further synthesis of examples of this substance class for the development of new drugs.

show abstract

Crystal structure of (Z)-1-(1,5-dimethyl-1H-pyrazol-3-yl)-3-hydroxy-3-(p-toly)prop-2-en-1-one, C₁₅H₁₆N₂O₂

Cited by 4 publications

References 11 publications

β-Keto-enol Tethered Pyridine and Thiophene: Synthesis, Crystal Structure Determination and Its Organic Immobilization on Silica for Efficient Solid-Liquid Extraction of Heavy Metals

β-Keto-enol Tethered Pyridine and Thiophene: Synthesis, Crystal Structure Determination and Its Organic Immobilization on Silica for Efficient Solid-Liquid Extraction of Heavy Metals

Novel β-keto–enol Pyrazolic Compounds as Potent Antifungal Agents. Design, Synthesis, Crystal Structure, DFT, Homology Modeling, and Docking Studies

Synthesis, Biochemical Characterization, and Theoretical Studies of Novel β-Keto-enol Pyridine and Furan Derivatives as Potent Antifungal Agents

Contact Info

Product

Resources

About