Crystal structure, physicochemical, DFT, optical, keto-enol tautomerization, docking, and anti-diabetic studies of (Z)-pyrazol β-keto-enol derivative

Tighadouini, Saïd; Roby, Othmane; Mortada, Salma; Lakbaibi, Zouhair; Radi, Smaail; Ali, Anas Al; Faouzi, My El Abbes; Ferbinţeanu, Marilena; Garcia, Yann; Al‐Zaqri, Nabil; Zarrouk, A.; Warad, Ismail

doi:10.1016/j.molstruc.2021.131308

Cited by 16 publications

(6 citation statements)

References 33 publications

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“…These findings were supported by one of the most well-known DFT indices [36], the nucleophilic Parr functions (P-) [37], which is a useful tool for assessing the potential nucleophilic compound sites. By adding an electron of the Mulliken atomic spin density at the radical cation, we obtain these functions.…”

Section: Methodsmentioning

confidence: 69%

Mesoporous Silica Modified with 2-Phenylimidazo[1,2-a] pyridine-3-carbaldehyde as an Effective Adsorbent for Cu(II) from Aqueous Solutions: A Combined Experimental and Theoretical Study

et al. 2022

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In this study, we will present an efficient and selective adsorbent for the removal of Cu(II) ions from aqueous solutions. The silica-based adsorbent is functionalized by 2-phenylimidazo[1,2-a] pyridine-3-carbaldehyde (SiN-imd-py) and the characterization was carried out by applying various techniques including FT-IR, SEM, TGA and elemental analysis. The SiN-imd-py adsorbent shows a good selectivity and high adsorption capacity towards Cu(II) and reached 100 mg/g at pH = 6 and T = 25 °C. This adsorption capacity is important compared to other similar adsorbents which are currently published. The adsorption mechanism, thermodynamics, reusability and the effect of different experimental conditions, such as contact time, pH and temperature, on the adsorption process, were also investigated. In addition, a theoretical study was carried out to understand the adsorption mechanism and the active sites of the adsorbent, as well as the stability of the complex formed and the nature of the bonds.

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Section: Methodsmentioning

confidence: 69%

Mesoporous Silica Modified with 2-Phenylimidazo[1,2-a] pyridine-3-carbaldehyde as an Effective Adsorbent for Cu(II) from Aqueous Solutions: A Combined Experimental and Theoretical Study

et al. 2022

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“…The latter has a big value as the binding energy of different isomeric forms to biomolecules depends greatly on the structure and the absolute configuration. Moreover, as was stated in previous works, understanding keto-enol tautomerism is significant in order to substantiate critical biological applications of the tautomeric molecules and to comprehend their biochemical reactions (Tighadouini et al, 2022;Temperini et al, 2009).…”

Section: Figurementioning

confidence: 83%

3,3′-(Phenylmethylene)bis(1-ethyl-3,4-dihydro-1H-2,1-benzothiazine-2,2,4-trione): single-crystal X-ray diffraction study, quantum-chemical calculations and Hirshfeld surface analysis

et al. 2023

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The title compound, C27H26N2O6S2, possesses potential antimicrobial, analgesic, and anti-inflammatory activity. This compound has three tautomeric forms, which relative energies were estimated with quantum-chemical calculations. All these tautomers (dienol form 7A, keto–enol form 7B, and diketo form 7C) were optimized by the M06–2X/cc-pVTZ method in a vacuum, using the PCM model with chloroform and DMSO as solvent. The diketo form of the title compound proved to be the most energetically favourable as compared to the keto–enol or dienol forms. The diketo form can exist as three possible stereoisomers with the same configuration of one stereogenic center and different configurations of the stereogenic centers at two other atoms: ( R , R , R ), (S , R , S ) and ( R , R , S ). The ( R , R , S ) stereoisomer was found in the crystal phase. It was revealed that the thiazine rings of equivalent benzothiazine fragments have different conformations, (a sofa or a half-chair). The two bicyclic fragments connected through the phenylmethylene group are oriented almost orthogonal to each other, subtending a dihedral angle of 82.16(7)°.

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“…The asymmetric unit consists of one nickel atom with three coordinated L1 ligands and two non-coordinating perchlorate counter-ions. The nickel centre is in a distorted octahedral environment [ffNÀ Ni-N = 76.97(6)-97.87 (7)°] composed of six nitrogen atoms of three bidentate ligands. The ligands are arranged in a way that the complex shows a 3-fold (C 3 ) Scheme 3.…”

Section: Resultsmentioning

confidence: 99%

“…Pyrazole-based precursors have raised great interest due to their use in a variety of fields with broad socio economic implications, such as pharmaceutics and biology, catalysis, corrosion inhibition, [1][2][3] and environmental studies. [4][5][6][7] The incorporation of a tetrazole ring to produce a pyrazole-tetrazole platform can lead to a variety of applications, based on medicinal chemistry, [8,9] catalysis, [10] energetic materials, [11,12] magnetism, [13] spin crossover, [14] chemical sensing, [15,16] luminescent properties, [17] to name but a few. On the other hand, metal complexes are gaining popularity as a promising alternative to traditional organic antibiotics.…”

Section: Introductionmentioning

confidence: 99%

High Inhibition for a Co^II Tetrazole Bi‐pyrazole Dinuclear Complex against Fusarium Oxysporum f. sp. Albedinis

Bahjou,

Radi,

El Massaoudi

et al. 2023

Eur J Inorg Chem

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New coordination compounds made of two novel tetrazole and C,N‐bipyrazole ligands, 2‐(3,5,5′‐trimethyl‐1′H‐[1,3′‐bipyrazol]‐1′‐yl)acetonitrile (L1), and 1′‐((1H‐tetrazol‐5‐yl)methyl)‐3,5,5′‐trimethyl‐1′H‐1,3′‐bipyrazole (HL2), were prepared and fully characterized by spectroscopic techniques. Their crystal structures were identified by single‐crystal X‐ray diffraction revealing mononuclear complexes: [Ni(L1)3](ClO4)2 (1), [Cd(L1)2Cl2] (2), [Cu(HL2)(L2)]ClO4 (3), [Cu(L2)2] (4) and a dinuclear complex [Co2(HL2)(L2)Cl3] (5) comprising CoII ions in octahedral and tetrahedral surrounding within the same unit. Noticeably, 3 and 4 show different architectural structures due to ligand deprotonation as well as the effect of the counter anion. All compounds demonstrated antimicrobial activity against Gram (+) bacteria Listeria innocua and Staphylococcus aureus, as well as Gram (−) bacteria such as Escherichia coli and Pseudomonas aeruginosa, and antifungal activity against pathogenic fungi Geotrichum candidum, Aspergillus niger, and Penicillium crustosum. Interestingly, a high inhibition activity of 97 % was reached for 5 with a low concentration of only 81.1 μmol/L against Fusarium oxysporum f. sp. Albedinis, which is commonly damaging palm trees crops.

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Crystal structure, physicochemical, DFT, optical, keto-enol tautomerization, docking, and anti-diabetic studies of (Z)-pyrazol β-keto-enol derivative

Cited by 16 publications

References 33 publications

Mesoporous Silica Modified with 2-Phenylimidazo[1,2-a] pyridine-3-carbaldehyde as an Effective Adsorbent for Cu(II) from Aqueous Solutions: A Combined Experimental and Theoretical Study

Mesoporous Silica Modified with 2-Phenylimidazo[1,2-a] pyridine-3-carbaldehyde as an Effective Adsorbent for Cu(II) from Aqueous Solutions: A Combined Experimental and Theoretical Study

3,3′-(Phenylmethylene)bis(1-ethyl-3,4-dihydro-1H-2,1-benzothiazine-2,2,4-trione): single-crystal X-ray diffraction study, quantum-chemical calculations and Hirshfeld surface analysis

High Inhibition for a Co^II Tetrazole Bi‐pyrazole Dinuclear Complex against Fusarium Oxysporum f. sp. Albedinis

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Crystal structure, physicochemical, DFT, optical, keto-enol tautomerization, docking, and anti-diabetic studies of (Z)-pyrazol β-keto-enol derivative

Cited by 16 publications

References 33 publications

Mesoporous Silica Modified with 2-Phenylimidazo[1,2-a] pyridine-3-carbaldehyde as an Effective Adsorbent for Cu(II) from Aqueous Solutions: A Combined Experimental and Theoretical Study

Mesoporous Silica Modified with 2-Phenylimidazo[1,2-a] pyridine-3-carbaldehyde as an Effective Adsorbent for Cu(II) from Aqueous Solutions: A Combined Experimental and Theoretical Study

3,3′-(Phenylmethylene)bis(1-ethyl-3,4-dihydro-1H-2,1-benzothiazine-2,2,4-trione): single-crystal X-ray diffraction study, quantum-chemical calculations and Hirshfeld surface analysis

High Inhibition for a CoII Tetrazole Bi‐pyrazole Dinuclear Complex against Fusarium Oxysporum f. sp. Albedinis

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High Inhibition for a Co^II Tetrazole Bi‐pyrazole Dinuclear Complex against Fusarium Oxysporum f. sp. Albedinis