New bis hydrazone: Synthesis, X-ray crystal structure, DFT computations, conformational study and in silico study of the inhibition activity of SARS-CoV-2

Tabbiche, Abdelkader; Bouchama, Abdelaziz; Chafai, Nadjib; Zaidi, Farouk; Chiter, Chaabane; Yahiaoui, Messaoud; Abiza, Abdellah

doi:10.1016/j.molstruc.2022.132865

Cited by 23 publications

(6 citation statements)

References 58 publications

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“…There are only a few reported crystal structures of Schiff bases derived from benzil (Tabbiche et al, 2022;Bouchama et al, 2007;Bai et al, 2006). We recently synthesized the title compound and we now report its crystal structure.…”

Section: Structure Descriptionmentioning

confidence: 96%

2-[(4-Chlorophenyl)imino]-1,2-diphenylethanone

Ziani¹,

Brihi²,

Kadri³

et al. 2023

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Section: Structure Descriptionmentioning

confidence: 96%

2-[(4-Chlorophenyl)imino]-1,2-diphenylethanone

Ziani¹,

Brihi²,

Kadri³

et al. 2023

IUCr Data

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“…The 13 C NMR spectra showed the signals corresponding to the carbon atom of azomethine group around δ = 149.3 ppm. Literature precedents show that conformational effects play an essential role in the biological activity of sulfonic esters [22,23] and hydrazones [24]. Moreover, the binding of a drug ligand to the target and the strength of the effect are related to its ability to adopt the right conformation to t into the target binding site [25].…”

Section: Chemistrymentioning

confidence: 99%

Synthesis, crystal structure, Hirshfeld surface analysis and bioactivity studies of the hydrazones derived from 2-methylsulfonyl-5-nitrobezaldehyde against the breast (MCF-7) and cervical (HeLa) cancer cell lines, and their antioxidant potential.

Maluleka,

Mphahlele

2024

Preprint

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The hydrazones derived from 2-formyl-4-nitrophenyl methanesulfonate were characterized using a combination of spectroscopic and single crystal X-ray diffraction (XRD) techniques, in turn, evaluated for cytotoxicity in vitro against the human breast adenocarcinoma (MCF-7) and human cervical cancer (Hela) cell lines. The presence of a chlorine atom on the para position of the phenylhydrazone moiety of 3b resulted in increased cytotoxicity compared to camptothecin (IC50 = 3.71 ± 0.16 µM and 9.15 ± 0.84 µM, respectively) against the Hela and MCF-7 cell lines with IC50 values of 2.40 ± 0.13 µM and 5.64 ± 0.84 µM, respectively. The hydrazone derivatives exhibited significant 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical scavenging activity compared to ascorbic acid and 2-formyl-4-nitrophenyl methanesulfonate. Increased interactions of the arylhydrazone moiety are predicted with the residues in the active site of tyrosine kinase and cytochrome c peroxidase.

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“…Although no clinical data are yet to establish the effectiveness of oseltamivir towards coronaviruses, studies have shown that hydrazone derivatives of compounds can possess interesting inhibitory activities towards coronaviruses especially as oseltamivir is used to treat viral-related issues. 28,29 Hydrazones are a highly versatile chemical moiety that can be modified in a number of ways to produce analogs with improved pharmacological properties. 30 The presence of the hydrazone functional group allows for the formation of various types of covalent and non-covalent interactions with target biomolecules, such as enzymes and receptors, which can lead to the modulation of their activity.…”

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Investigation of Methyl-5-(pentan-3-yloxy)-7-oxabicyclo[4.1.0]hept-3-ene-3-carboxyhydrazide Derivatives as Potential Inhibitors of COVID-19 Main Protease: DFT and Molecular Docking Study

Akinyele,

Fakola,

Adeboye

et al. 2023

Bioinform Biol Insights

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The search for effective therapeutics to combat COVID-19 has led to the exploration of the biological activity of numerous compounds. In this study, hydrazones derived from oseltamivir intermediate, methyl 5-(pentan-3-yloxy)-7-oxabicyclo[4.1.0]hept-3-ene-3-carboxylate have been investigated for their potential as drug candidates against the COVID-19 virus using computational methods, including density functional theory (DFT) studies, molecular docking, and absorption, distribution, metabolism, excretion and toxicity (ADMET) analysis. The DFT studies provide information on the electronic properties of the compounds while the molecular docking results using AutoDock reported the binding energies between the main protease of COVID-19 and the compounds. The DFT results revealed that the energy gap of the compounds ranged from 4.32 to 5.82 eV while compound HC had the highest energy gap (5.82 eV) and chemical potential (2.90 eV). The electrophilicity index values of the 11 compounds ranged from 2.49 to 3.86, thus they were classified as strong electrophiles. The molecular electrostatic potential (MESP) revealed electron-rich and electron-deficient regions of the compounds. The docking results reveal that all the compounds had better docking scores than remdesivir and chloroquine, frontline drugs employed in combating COVID-19, with HC having the best docking score of -6.5. The results were visualized using Discovery studio, which revealed hydrogen bonding, pi-alkyl interaction, alkyl interaction, salt bridge interaction, halogen interaction as being responsible for the docking scores. The drug-likeness results showed that the compounds qualify as oral drug candidates as none of them violated Vebers and Lipinski’s rule. Thus, they could serve as potential inhibitors of COVID-19.

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New bis hydrazone: Synthesis, X-ray crystal structure, DFT computations, conformational study and in silico study of the inhibition activity of SARS-CoV-2

Cited by 23 publications

References 58 publications

2-[(4-Chlorophenyl)imino]-1,2-diphenylethanone

2-[(4-Chlorophenyl)imino]-1,2-diphenylethanone

Synthesis, crystal structure, Hirshfeld surface analysis and bioactivity studies of the hydrazones derived from 2-methylsulfonyl-5-nitrobezaldehyde against the breast (MCF-7) and cervical (HeLa) cancer cell lines, and their antioxidant potential.

Investigation of Methyl-5-(pentan-3-yloxy)-7-oxabicyclo[4.1.0]hept-3-ene-3-carboxyhydrazide Derivatives as Potential Inhibitors of COVID-19 Main Protease: DFT and Molecular Docking Study

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