Synthesis and antimicrobial evaluation of new halogenated 1,3-Thiazolidin-4-ones

Hammad, Shaymaa G.; El‐Gazzar, Marwa G.; Abutaleb, Nader S.; Li, Daoyi; Ramming, Isabell; Shekhar, Aditya; Abdel‐Halim, Mohammad; Elrazaz, Eman Z.; Seleem, Mohamed N.; Bilitewski, Ursula; Abouzid, Khaled A. M.; El‐Hossary, Ebaa M.

doi:10.1016/j.bioorg.2019.103517

Cited by 18 publications

(23 citation statements)

References 77 publications

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“…Compounds containing the thiazolidin-4-one core exhibit varied bioactivities as anticonvulsives [18], antileukemics [19], antibacterials [20,21], and antitumorals [22], among others. The introduction of moieties with known biological activity, such as pyrimidine and pyrazole rings, is a good strategy in drug design, since those cores occupy an important place in heterocyclic chemistry as well as in medicinal chemistry, because of the wide range of chemical [23,24], industrial and pharmacological properties they possess [25,26,27,28].…”

Section: Introductionmentioning

confidence: 99%

Computer-aided design, synthesis, and characterization of molecular hybrids of dihydropyrazoles, aminopyrimidines, and thiazolidin-4-ones as potential inhibitors of the penicillin-binding protein 3 (PBP-3) of Escherichia coli

Orozco-Lopez¹,

Guerrero-Villalobos

Cuervo-Pardo

2021

Univ. Sci.

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A computer-assisted approach was used to model and study privileged heterocyclic scaffolds containing dihydropyrazole, pyrimidin-2-amine, and thiazolidin-4-one moieties (hybrid pharmacophores) to obtain novel and promising antimicrobial prototype molecules. Main bioavailability descriptors were determined in order to assess the drug-likeness of the designed compounds and to pre-filter eleven compounds exhibiting the best profiles, thus passing to molecular docking study against a key penicillin-binding protein type-3 from enterotoxygenic E. coli. Seven structures were chosen by theirenergies of affinity and docking interactions with key residues in the active site of the receptor. Seven compounds with the highest docking scores belonging to the series of chalcones, dihydropyrazoles, aminopyrimidines, and thiazolidin-4-ones were prepared via condensation or cyclocondensation reactions. The structural elucidation of the final products was carried out by infrared spectra analysis and NMR experiments. Such molecular hybrids considered as potential hits in the search for new antibacterial compounds will be tested in vitro in further studies.

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Section: Introductionmentioning

confidence: 99%

Computer-aided design, synthesis, and characterization of molecular hybrids of dihydropyrazoles, aminopyrimidines, and thiazolidin-4-ones as potential inhibitors of the penicillin-binding protein 3 (PBP-3) of Escherichia coli

Orozco-Lopez¹,

Guerrero-Villalobos

Cuervo-Pardo

2021

Univ. Sci.

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“…Microbial resistance is acquired via different mechanisms such as the overexpression of antibiotic-inactivating enzymes (e.g. extended-spectrum β-lactamases (ESBL)producing Enterobacteriaceae), mutations of the outer membrane or target enzymes as well as enhanced activity of efflux pumps [7][8][9]. However, the Egyptian Journal of Chemistry http://ejchem.journals.ekb.eg/ _____________________________________________________________________________________________________________ ________________________________________________ Egypt.…”

Section: Introductionmentioning

confidence: 99%

“…Studies showed that DNA topoisomerases enzymes regulate DNA topology via cleaving and rejoining DNA strands. They introduce a crucial role to regulate the physiological actions of the genome [1][2][3] in addition to DNA activities such as replication, transcription [4][5][6], recombination [7,8], repair [9,10], chromosome decondensation and sister chromatid [11,12]. DNA gyrase and topoisomerase IV are type II topoisomerases [13,14].…”

Section: Introductionmentioning

confidence: 99%

Design, Synthesis and Molecular Docking of New Benzimidazole Derivatives of Potential Antimicrobial Activity as DNA Gyrase and Topoisomerase IV Inhibitors

et al. 2021

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A new series of benzimidazole derivatives 3a-3d, 4a-4c, 8a-8d, 9a,9b, 10a-10d and 11 was synthesized and evaluated as antimicrobial agents against various gram-positive, gram-negative bacteria and fungi using vibramycin and fluconazole as positive controls for the antibacterial and antifungal activities, respectively. The examined microbial strains showed variable sensitivities against the target compounds.The examined microbial strains showed variable sensitivities against the target compounds. The minimum inhibitory concentration (MIC) was determined for the compounds showed zone of inhibition ≥ 16 mm (4a, 4c, 8a, 10a). The latter derivatives were also examined as S. aureus DNA gyrase/topoisomerase IV inhibitors. The compounds 4a, and 8a represented the most promising activity for both enzymes in ATPase assay (IC50 4a 0.39, 0.52 and 8a 0.66, 0.28 µM respectively) as well as the safest profile against the human normal WI38 cells upon comparing with Ciprofloxacin and Novobiocin. Compounds 8a showed dual inhibitory effect against both targets DNA gyrase and topoisomerase IV in supercoiling and decatenation assay (IC50 0.443 and 1.15 µM respectively). Both compounds 4a and 8a can be considered as lead compounds for further structural modifications to obtain more potent DNA gyrase and topoisomerase inhibitors as antibacterial agents. Molecular docking study was performed for the most promising compounds to explore the pharmacophoric moieties that governed their binding with amino acid residues of DNA gyrase and topoisomerase IV using MOE software. The results revealed a binding mode and docking scores comparable to those of a reference ligand and consistent with their DNA gyrase and topoisomerase IV inhibition activity.

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“…E. coli, S. aureus and K. pneumonia show resistance towards multiple drugs as they can highly adapt themselves to the hosts and healthcare conditions [6]. This challenging problem makes the antimicrobial treatment become ineffective leading to increased treatment costs and higher disease morbidity and mortality particularly in immunocompromised patients [7]. Therefore, novel antibacterial compounds with novel targets and selective toxicity need to be developed to overcome this problem [6,7].…”

Section: Introductionmentioning

confidence: 99%

“…This challenging problem makes the antimicrobial treatment become ineffective leading to increased treatment costs and higher disease morbidity and mortality particularly in immunocompromised patients [7]. Therefore, novel antibacterial compounds with novel targets and selective toxicity need to be developed to overcome this problem [6,7]. DNA gyrase and topoisomerase IV are type II topoisomerases play a vital role DNA replication and repair thus, they are crucial for cell viability and offer the opportunity to develop novel antibacterial candidates which can overcome the bacterial resistance obstacle [8].…”

Section: Introductionmentioning

confidence: 99%

Convenient synthesis of new indeno[1,2-b]pyridine derivatives for antimicrobial and antioxidant evaluation

Kotb¹,

Soliman²,

M.M.Hassan³

et al. 2020

Egypt. J. Chem.

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A new set of 1H-indenopyrdine-based derivatives were synthesized using the compound 4-(4-hydroxy-3methoxyphenyl)-2-oxo-2,5-dihydro-1H-indeno[1,2-b]pyridine-3-carbonitrile (1) as the key starting compound. The molecular structures of the new derivatives were identified using various spectroscopic techniques and elemental analysis. All the new analogues were screened as antimicrobial against different strains of Gram +ve, Gram -ve bacteria and the opportunistic pathogenic yeast C. albicans. Some of the new indenopyrdines exhibited moderate antimicrobial activity comparing to gentamicin as a standard drug. On the reverse, the free radical scavenging activity of the new compounds using DPPH assay protocol revealed that most of the compounds were potent antioxidant agents while comparing to ascorbic acid as a positive antioxidant control.

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Synthesis and antimicrobial evaluation of new halogenated 1,3-Thiazolidin-4-ones

Cited by 18 publications

References 77 publications

Computer-aided design, synthesis, and characterization of molecular hybrids of dihydropyrazoles, aminopyrimidines, and thiazolidin-4-ones as potential inhibitors of the penicillin-binding protein 3 (PBP-3) of Escherichia coli

Computer-aided design, synthesis, and characterization of molecular hybrids of dihydropyrazoles, aminopyrimidines, and thiazolidin-4-ones as potential inhibitors of the penicillin-binding protein 3 (PBP-3) of Escherichia coli

Design, Synthesis and Molecular Docking of New Benzimidazole Derivatives of Potential Antimicrobial Activity as DNA Gyrase and Topoisomerase IV Inhibitors

Convenient synthesis of new indeno[1,2-b]pyridine derivatives for antimicrobial and antioxidant evaluation

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