Synthesis, X-ray crystallographic study and molecular docking of new α-sulfamidophosphonates: POM analyses of their cytotoxic activity

Bechlem, Khaoula; Aissaoui, Mohamed; Belhani, Billel; Rachedi, Khadidja Otmane; Bouacida, Sofiane; Bahadi, Rania; Djouad, Seif‐Eddine; Mansour, Riadh Ben; Bouaziz, Mohamed; Almalki, Faisal A.; Hadda, Taïbi Ben; Berredjem, Malika

doi:10.1016/j.molstruc.2020.127990

Cited by 38 publications

(14 citation statements)

References 41 publications

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“…Molecular geometry the gas phase structure optimization of sulfamoyloxy-oxazolidinones derivatives (1-10)C is optimized using DFT at B3LYP method [ 37 , 38 ], with the basis set of 6–31 G (d,p) implemented by Gaussian 09 package [ 39 , 40 ]. Frontier molecular orbitals and global reactivity descriptors the highest occupied molecular orbital (HOMO) and lowest un- occupied molecular orbital (LUMO) [41] , energy gap and chemical reactivity descriptors are calculated at DFT/B3LYP/6-31 G (d, p) method.…”

Section: Methodsmentioning

confidence: 99%

Synthesis, in silico study (DFT, ADMET) and crystal structure of novel sulfamoyloxy-oxazolidinones: Interaction with SARS-CoV-2

Bouzina

Berredjem

Bouacida

et al. 2022

Journal of Molecular Structure

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A new series of sulfamoyloxyoxazolidinone (SOO) derivatives have been synthesized and characterized by single-crystal X-ray diffraction, NMR, IR, MS and EA. Chemical reactivity and geometrical characteristics of the target compounds were investigated using DFT method. The possible binding mode between SOO and Main protease (Mpro) of SARS-CoV-2 and their reactivity were studied using molecular docking simulation. Single crystal X-ray diffraction showed that SOO crystallizes in a monoclinic system with P 2 1 space group. The binding energy of the SARS-CoV-2/Mpro-SOO complex and the calculated inhibition constant using docking simulation showed that the active SOO molecule has the ability to inhibit SARS-CoV2. We studied the prediction of absorption, distribution, properties of metabolism, excretion and toxicity (ADMET) of the synthesized molecules.

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Section: Methodsmentioning

confidence: 99%

Synthesis, in silico study (DFT, ADMET) and crystal structure of novel sulfamoyloxy-oxazolidinones: Interaction with SARS-CoV-2

Bouzina

Berredjem

Bouacida

et al. 2022

Journal of Molecular Structure

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“…Bechelem et al [91] carried out a theoretical study by POM bioinformatics analysis and molecular docking which consisted in identifying the pharmacophores sites of some previous sulfamidophosphonates. The results displayed two combined significant antiviral/antifungal O,O-pharmacophore sites.…”

Section: Previous Laboratory Workmentioning

confidence: 99%

Recent Advances in the Synthesis of α‐Aminophosphonates: A Review

et al. 2021

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α-Aminophosphonates play an important role across several fields, including organic synthesis and various potential applications. This review paper surveys recent achievements in the synthesis of α-Aminophosphonates, it summarizes the main synthetic routes towards α-Aminophosphonates that are known and it describes their biological proprieties from January2010 till December 2020: Special attention is devoted to green chemical approaches including catalysts, ultrasonic and microwave irradiations. We hope this paper will be a useful resource for researchers and that it will help them to work in this emerging research area.

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“…POM physicochemical analysis or ADME/T is important to qualify drugs and their efficacy as leading candidates against various biotargets, as like antibacterial (Grib et al, 2020;Hatzade et al, 2015;Jamalis et al, 2020;Jarrahpour et al,2019;Mabkhot et al, 2015Mabkhot et al, , 2016Messali et al, 2014Messali et al, , 2015Nasruddin et al, 2018;Rad et al, 2017;Rbaa et al, 2019;Sajid et al, 2016;Tatar et al, 2016), antifungal (Al-Maqtari et al, 2017Khan et al, 2017;Rachedi et al, 2020;Radi et al, 2015;Tighadouni et al, 2016;Titi et al, 2019), antiviral (Chander et al, 2017;Lahsasni et al, 2015), antitumoral (Bechlem et al, 2020;Kamal et al, 2019;Piaz et al, 2018;Rachedi et al, 2019Rachedi et al, , 2020Youssoufi et al, 2015), antiparasitic drugs and various enzymes inhibitors (Amirkhanov et al, 2019;Ben Hadda et al, 2018Mabkhot et al, 2014;Rauf et al, 2017). The POM physicochemical calculations included a partition coefficient (cLogP), aqueous solubility, donor hydrogen bond, and drug-likeness, evaluated in terms of Lipinski's ruleof-five.…”

Section: Pom Analyses and Identification Of Pharmacophore Sitesmentioning

confidence: 99%

How to face COVID-19: proposed treatments based on remdesivir and hydroxychloroquine in the presence of zinc sulfate. Docking/DFT/POM structural analysis

Hadda

Berredjem

Almalki

et al. 2021

Journal of Biomolecular Structure and Dynamics

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Remdesivir and hydroxychloroquine derivatives form two important classes of heterocyclic compounds. They are known for their anti-malarial biological activity. This research aims to analyze the physicochemical properties of remdesivir and hydroxychloroquine compounds by the computational approach. DFT, docking, and POM analyses also identify antiviral pharmacophore sites of both compounds. The antiviral activity of hydroxychloroquine compound's in the presence of zinc sulfate and azithromycin is evaluated through its capacity to coordinate transition metals (M = Cu, Ni, Zn, Co, Ru, Pt). The obtained bioinformatic results showed the potent antiviral/antibacterial activity of the prepared mixture (Hydroxychloroquine/Azithromycin/Zinc sulfate) for all the opportunistic Gram-positive, Gram-negative in the presence of coronavirus compared with the complexes Polypyridine-Ruthenium-di-aquo. The postulated zinc(II) complex of hydroxychloroquine derivatives are indeed an effective antibacterial and antiviral agent against coronavirus and should be extended to other pathogens. The combination of a pharmacophore site with a redox [Metal(OH 2 ) 2 ] moiety is of crucial role to fight against viruses and bacteria strains. Communicated by Ramaswamy H. Sarma

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Synthesis, X-ray crystallographic study and molecular docking of new α-sulfamidophosphonates: POM analyses of their cytotoxic activity

Cited by 38 publications

References 41 publications

Synthesis, in silico study (DFT, ADMET) and crystal structure of novel sulfamoyloxy-oxazolidinones: Interaction with SARS-CoV-2

Synthesis, in silico study (DFT, ADMET) and crystal structure of novel sulfamoyloxy-oxazolidinones: Interaction with SARS-CoV-2

Recent Advances in the Synthesis of α‐Aminophosphonates: A Review

How to face COVID-19: proposed treatments based on remdesivir and hydroxychloroquine in the presence of zinc sulfate. Docking/DFT/POM structural analysis

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