Microwave-assisted synthesis, molecular docking and anti-HIV activities of some drug-like quinolone derivatives

Jassem, Ahmed Majeed; Dhumad, Adil Muala; Almashal, Faeza Abdul Kareem; Alshawi, Jasim

doi:10.1007/s00044-020-02546-z

Cited by 24 publications

(9 citation statements)

References 50 publications

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“…Protein–ligand docking has proved to be a powerful tool for investigating and providing a proper information about protein‐ligand interactions in order to help the design of potentially active hits compounds [29] . In our search for design of new compounds as anti‐HIV inhibitors, we have selected compound 5 f (as it showed a potency against HIV‐1 replication) for the docking modelling study.…”

Section: Resultsmentioning

confidence: 99%

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Synthesis, Antimicrobial Activity, Anti‐HIV Activity, and Molecular Docking of Novel 5‐, 6‐ and 7‐Membered Ring (1H‐Pyrrol‐2‐yl)aminolactams

Jassem

Dhumad

2021

ChemistrySelect

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An efficient method has been developed for the synthesis of novel 5‐, 6‐ and 7‐membered ring (1H‐pyrrol‐2‐yl)aminolactams 5 a–f. This method featured Ugi‐4‐center‐3‐component reaction (U4 C3 C) followed by a post‐transformation reaction. All the newly synthesized (1H‐pyrrol‐2‐yl)aminolactams 5 a–f have been screened against six microbial species and the results revealed that these lactams exhibited moderate to good activity. These lactams were also tested in an in vitro for their antiviral activity against of HIV‐1 and HIV‐2 replication using MT‐4 cells. The testing results showed that compound 5 f is the only compound in the set lactams exhibiting a significant inhibition against HIV‐1 replication in cell line with EC50 value of 2.74±1.08 μM (CC50 of 18.93±4.0 μM), and SI 6. In addition, the compound 5 f was docked with essential proteins of HIV‐1 and HIV‐2 reverses transcriptase (RT), including HIV‐1 and HIV‐2 integrases strand proteins (PDB ID: 1EP4, 1FK9, 1HNV, 1VRU, 3DLE, 3DLG, and 3MEC). The docking results revealed that important hydrogen bond interactions and hydrophobic interactions were found between the compound 5 f and the essential amino acids residues of HIV‐1 and HIV‐2 (RT) proteins.

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Section: Resultsmentioning

confidence: 99%

“…PyMOL molecular graphic program (version 2.0 Schrödinger, LLC) is used to visualize the molecules and generate qualitative structural pictures of these molecules [29] . The PyMOL plugin provides multiple advanced rendering options and exceptional 3D viewing functionalities into a platform that is very important in drug design [31] .…”

Section: Resultsmentioning

confidence: 99%

Synthesis, Antimicrobial Activity, Anti‐HIV Activity, and Molecular Docking of Novel 5‐, 6‐ and 7‐Membered Ring (1H‐Pyrrol‐2‐yl)aminolactams

Jassem

Dhumad

2021

ChemistrySelect

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“…The production of isoindolinone derivatives requires various procedures, with expensive catalysts, prolonged reaction periods, and hazardous organic solvents needed for some. − Meanwhile, microwave (MW) irradiation has been commonly utilized for organic synthesis. − In fact, over the past decade, MW radiation has become a popular energy source in organic synthesis. Different approaches − have been utilized for isoindolinone derivative synthesis, although they often entail higher costs, longer wait times, and the use of toxic solvents. The green novel method for organic synthesis, the MW heating strategy, boasts high yields and quick reaction times, minimizing the formation of byproducts and increasing product purities.…”

Section: Introductionmentioning

confidence: 99%

Copper-Catalyzed Asymmetric Hydroboration Reaction of Novel Methylene Isoindolinone Compounds through Microwave Irradiation and Their Antileishmanial and Antitoxoplasma Activities

et al. 2023

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The aim of this study was devoted into molecular docking calculations to discover the potential antileishmania and antitoxoplasma activities of newly synthesized compounds obtained by applying a practical and simple method under microwave irradiation. All these compounds were tested in vitro for their biological activity against Leishmania major promastigotes, amastigotes, and Toxoplasma gondii tachyzoites. Compounds 2a, 5a, and 5e were the most active against both L. major promastigotes and amastigotes, with IC 50 values of less than 0.4 μM mL −1 . Compounds 2c, 2e, 2h, and 5d had a strong antitoxoplasma activity of less than 2.1 μM mL −1 against T. gondii. We can conclude that aromatic methyleneisoindolinones are potently active against both L. major and T. gondii. Further studies for mode of action evaluation are recommended. Compounds 5c and 5b are the best drug candidates for antileishmania and antitoxoplasma due to their SI values being over 13. The docking studies of compounds 2a-h and 5a-e against pteridine reductase 1 and T. gondii enoyl acyl carrier protein reductase reveal that compound 5e may be an effective antileishmanial and antitoxoplasma drug discovery initiative.

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“…This makes it possible to use them in the therapy of bacterial pneumonia related to COVID-19, as long as the pandemic is still in progress and the special treatment has not yet been created. Moreover, new derivatives reveal antiviral [ 10 ], antifungal [ 11 ], anticancer [ 12 , 13 ], anti-inflammatory [ 14 ] and hypoglycemic [ 15 ] activity. That is why fluoroquinolone molecules are promising objects in the search for new biologically active compounds.…”

Section: Introductionmentioning

confidence: 99%

A Comprehensive Review on Chemical Synthesis and Chemotherapeutic Potential of 3-Heteroaryl Fluoroquinolone Hybrids

et al. 2023

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Fluoroquinolones have been studied for more than half a century. Since the 1960s, four generations of these synthetic antibiotics have been created and successfully introduced into clinical practice. However, they are still of interest for medicinal chemistry due to the wide possibilities for chemical modification, with subsequent useful changes in the pharmacokinetics and pharmacodynamics of the initial molecules. This review summarizes the chemical and pharmacological results of fluoroquinolones hybridization by introducing different heterocyclic moieties into position 3 of the core system. It analyses the synthetic procedures and approaches to the formation of heterocycles from the fluoroquinolone carboxyl group and reveals the most convenient ways for such procedures. Further, the results of biological activity investigations for the obtained hybrid pharmacophore systems are presented. The latter revealed numerous promising molecules that can be further studied to overcome the problem of resistance to antibiotics, to find novel anticancer agents and more.

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Microwave-assisted synthesis, molecular docking and anti-HIV activities of some drug-like quinolone derivatives

Cited by 24 publications

References 50 publications

Synthesis, Antimicrobial Activity, Anti‐HIV Activity, and Molecular Docking of Novel 5‐, 6‐ and 7‐Membered Ring (1H‐Pyrrol‐2‐yl)aminolactams

Synthesis, Antimicrobial Activity, Anti‐HIV Activity, and Molecular Docking of Novel 5‐, 6‐ and 7‐Membered Ring (1H‐Pyrrol‐2‐yl)aminolactams

Copper-Catalyzed Asymmetric Hydroboration Reaction of Novel Methylene Isoindolinone Compounds through Microwave Irradiation and Their Antileishmanial and Antitoxoplasma Activities

A Comprehensive Review on Chemical Synthesis and Chemotherapeutic Potential of 3-Heteroaryl Fluoroquinolone Hybrids

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