Synthesis, spectroscopic characterization, crystal structure, DFT, ESI-MS studies, molecular docking and in vitro antibacterial activity of 1,5-benzodiazepin-2-one derivatives

Chkirate, Karim; Akachar, Jihane; Hni, Brahim; Hökelek, Tuncer; Anouar, El Hassane; Talbaoui, Ahmed; Mague, Joel T.; Sebbar, Nada Kheira; Ibrahimi, Azeddine; Essassi, El Mokhtar

doi:10.1016/j.molstruc.2021.131188

Cited by 17 publications

(9 citation statements)

References 44 publications

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“…To compare the activities of molecules against antioxidant proteins and discover novel and potent compounds for their antioxidant properties, molecular docking calculations were conducted. The Maestro Molecular modeling platform (version 12.8) by Schrödinger [17,18] was used for these calculations. Several modules, including protein preparation [19,20], LigPrep [21,22], and Glide ligand docking [23,24] were employed in the molecular docking calculations.…”

Section: Methodsmentioning

confidence: 99%

Liver cancer Properties of Extract of Atropa Belladonna L.

2023

Proceeding Book of 2nd International Conference on Contemporary Academic Research ICCAR 2023

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Atropa belladonna L., commonly known as deadly nightshade, is a perennial plant belonging to the Solanaceae family. It is native to central and southern Europe and is cultivated in various regions worldwide. This plant is renowned for being a significant source of tropane alkaloids within the Solanaceae family. In this study, the aim was to analyze the chemical composition of the methanol extract obtained from Atropa belladonna L. using the maceration method. The chemical components were identified through GC-MS analysis. Following the determination of these chemical constituents, their inhibitory activities against the Crystal structures of vascular endothelial growth factor (VEGF) receptors (PDB ID: 3WZE) and Deleted in Liver Cancer 2 (PDB ID: 2H80) for liver cancer, which were downloaded from the Protein Data Bank site, will be compared. This research aims to explore the potential of these chemical constituents as inhibitors for these specific protein targets in the context of liver cancer.

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Section: Methodsmentioning

confidence: 99%

Liver cancer Properties of Extract of Atropa Belladonna L.

2023

Proceeding Book of 2nd International Conference on Contemporary Academic Research ICCAR 2023

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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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“…The chemical structure was validated by the single-crystal Xray diffraction method, and an optimized structure was obtained using DFT and Hartree-Fock (HF) approaches. A wide range of calculations using DFT helps develop a close relationship between theoretical and experimental data by giving clues related to molecular geometry, electrical, and spectroscopic properties [18]. Theoretical computational techniques have become very reliable in predicting the properties of molecules with great precision [19][20][21].…”

Section: Introductionmentioning

confidence: 99%

Synthesis, crystal structure, DFT/HF, Hirshfeld surface, and molecular docking analysis of 4-(tert-butyl)-4-nitro-1,1-biphenyl

et al. 2023

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4-(tert-Butyl)-4-nitro-1,1-biphenyl has been synthesized, and its structure has been characterized by using some spectroscopic and single-crystal X-ray diffraction techniques. It crystallizes in a monoclinic crystal system with space group P21/n and unit cell parameters: a = 6.4478(3) Å, b = 9.2477(4) Å, c = 23.4572(9) Å, β = 95.114(4)°, V = 1393.11(10) Å3, Z = 4. The molecular structure has been solved by using the intrinsic phasing method. The crystal structure is stabilized by C-H···O interactions. Computational studies were performed using density functional theory (DFT) and Hartree-Fock (HF) methods. The optimized geometry obtained from DFT and HF in the gas phase was compared with solid-phase experimental data retrieved from single-crystal X-ray diffraction results. Frontier molecular orbitals, such as the HOMO/LUMO energy gap, the molecular electrostatic potential, and Mulliken atomic charges, have been investigated. The HOMO LUMO energy gap of 3.97 eV indicates that the molecule is soft and highly reactive. The Hirshfeld surface analysis and their associated fingerprint plots have been used to quantitatively validate the interactions. Further insilico molecular docking studies have been performed with the molecular target Type-II topoisomerase (PDB ID: 1JIJ) and their results suggest that 4-(tert-butyl)-4-nitro-1,1-biphenyl could be considered an anticancer drug.

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Synthesis, spectroscopic characterization, crystal structure, DFT, ESI-MS studies, molecular docking and in vitro antibacterial activity of 1,5-benzodiazepin-2-one derivatives

Cited by 17 publications

References 44 publications

Liver cancer Properties of Extract of Atropa Belladonna L.

Liver cancer Properties of Extract of Atropa Belladonna L.

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

Synthesis, crystal structure, DFT/HF, Hirshfeld surface, and molecular docking analysis of 4-(tert-butyl)-4-nitro-1,1-biphenyl

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