Synthesis, spectroscopic characterization, DFT, molecular docking and in vitro antibacterial potential of novel quinoline derivatives

Bouzian, Younos; Sert, Yusuf; Karrouchi, Khalid; Meervelt, Luc Van; Chkirate, Karim; Mahi, Lhassane; Ahabchane, Noureddine Hamou; Talbaoui, Ahmed; Essassi, El Mokhtar

doi:10.1016/j.molstruc.2021.131217

Cited by 17 publications

(4 citation statements)

References 51 publications

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“…Calculated numerical values for the title compound including electronegativity (χ), hardness (η), ionization potential (I), dipole moment (µ), electron affinity (A), electrophilicity (ω), and softness (σ) are collated in Table 3. Among the calculated parameters of the molecules, the highest occupied molecular orbital (HOMO) and lowest unoccupied molecular orbital (LUMO) parameters are more important than the others [26,27]. The electron transition from the HOMO to the LUMO energy level is shown in Figure 7…”

Section: Density Functional Theory Calculationsmentioning

confidence: 99%

2-(N-allylsulfamoyl)-N-propylbenzamide

El mahmoudi,

Chkirate,

Mokhi

et al. 2023

Molbank

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In this work, a new compound, 2-(N-allylsulfamoyl)-N-propylbenzamide, has been synthesized via a tandem one-pot reaction under sonication. The rotational orientations of the allylsulfamoyl and the amide groups in the title molecule, C13H18N2O3S, are partly determined by an intramolecular N—H···O hydrogen bond. In the crystal, a layer structure is generated by N—H···O and C—H···O hydrogen bonds plus C—H···π (ring) interactions. A Hirshfeld surface analysis indicates that the most important contributions to crystal packing are from H···H (59.2%), H···O/O···H (23.5%), and H···C/C···H (14.6%) interactions. The optimized structure calculated using density functional theory at the B3LYP/6–311 G (d,p) level is compared with the experimentally determined structure in the solid state. The calculated highest occupied molecular orbital (HOMO) and lowest unoccupied molecular orbital (LUMO) energy gap is 5.3828 eV.

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Section: Density Functional Theory Calculationsmentioning

confidence: 99%

2-(N-allylsulfamoyl)-N-propylbenzamide

El mahmoudi,

Chkirate,

Mokhi

et al. 2023

Molbank

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“…Calculated numerical values for the title compound, including electronegativity (χ), hardness (η), ionization potential (I), dipole moment (µ), electron affinity (A), electrophilicity (ω), and softness (σ), are collated in Table 2. Among the calculated parameters of the molecules, the highest occupied molecular orbital (HOMO) and lowest unoccupied molecular orbital (LUMO) parameters are more important than the others [41,42]. The electron transition from the HOMO to the LUMO energy level is shown in Figure 8 values for the title compound, including electronegativity (χ), hardness (η), ionization potential (I), dipole moment (μ), electron affinity (A), electrophilicity (ω), and softness (σ), are collated in Table 2.…”

Section: Density Functional Theory Calculationsmentioning

confidence: 99%

“…The electron transition from the HOMO to the LUMO energy level is shown in Figure 8 values for the title compound, including electronegativity (χ), hardness (η), ionization potential (I), dipole moment (μ), electron affinity (A), electrophilicity (ω), and softness (σ), are collated in Table 2. Among the calculated parameters of the molecules, the highest occupied molecular orbital (HOMO) and lowest unoccupied molecular orbital (LUMO) parameters are more important than the others [41,42]. The electron transition from the HOMO to the LUMO energy level is shown in…”

Section: Density Functional Theory Calculationsmentioning

confidence: 99%

2-((3-(4-Methoxyphenyl)-4,5-dihydroisoxazol-5-yl)methyl)benzo[d]isothiazol-3(2H)-one1,1-dioxide

Mahmoudi

Chkirate

Tachallait

et al. 2022

Molbank

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In this work, a novel compound N-(3-(4-methoxyphenyl)isoxazolin-5-yl)methylsaccharin has been synthesized. The molecular structure of the compound was determined using various spectroscopic techniques and confirmed by a single-crystal X-ray diffraction analysis. In the single crystal, C–H…O hydrogen bonds between neighboring molecules form chains along the a-axis direction. Hirshfeld surface analysis indicates that the most important contributions to the crystal packing are from H…H (35.7%), H…O/O…H (33.7%), and H…C/C…H (13%) interactions. The optimized structure calculated using density functional theory at the B3LYP/6–311 G(d,p) level is compared with the experimentally determined structure in the solid state. The calculated highest occupied molecular orbital (HOMO) and lowest unoccupied molecular orbital (LUMO) energy gap is 4.9266 eV.

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“…Quinoline derivatives possess number of medicinal properties like anti-bacterial [1] anti-filarial [2] anti-malarial [3,4] anti-fungal [5] cardiovascular [1] anti-tuberculosis [6]. 8-hydroxy quinoline derivative can be used as an active compound of pharmaceutical products [7] nuclear medicine [8] treating cancer [1] and neurodegeneration disorder [9].…”

Section: Introductionmentioning

confidence: 99%