Novel quinoline/thiazinan-4-one hybrids; design, synthesis, and molecular docking studies as potential anti-bacterial candidates against MRSA

Mohamed, Asmaa H.; Mostafa, Sara M.; Aly, Ashraf A.; Hassan, Alaa A.; Osman, Esraa M.; Nayl, A.A.; Brown, Alan B.; Abdelhafez, El Shimaa M.N.

doi:10.1039/d3ra01721d

Cited by 6 publications

(3 citation statements)

References 47 publications

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“…Schiff bases derived from benzothiazoles 5a-5j were assessed for their in-vitro antibacterial effects 27,28 against three distinct strains: S. aureus, S. epidermidis, and E. coli. This evaluation was conducted using the disc plate method.…”

Section: Antimicrobial Activitymentioning

confidence: 99%

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Synthesis, Characterisation, Molecular Docking Studies and Biological Evaluation of Novel Benzothiazole Derivatives as EGFR Inhibitors for Anti-breast Cancer Agents

Priya M,

Devhare,

Dharmamoorthy

et al. 2023

IJPQA

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Novel (2-anilino-N-(4,6-dimethyl-1,3-Benzosulfonazol-2-yl) ethanamide derivatives were synthesized and characterized by spectroscopy methods. All the compounds assessed for in-vitro antimicrobial activities on three strains are S. aureus, S. epidermis and E. coli by using disc plate method (25 μg/mL). Compounds 5a-5j showed good to excellent antimicrobial activity for three different strains compared to standard ciprofloxacin. Further screened by in-vitro cytotoxic activity against MCF-7 cell lines. Some compounds were 5i, 5c, 5b,5d and 5i showed high cytotoxic activities of IC50 values 73, 53,37,32 and 24 μg/mL, reference drug as Gefitinib against MCF-7 cell lines and MCF-12A. Further carried out docking studies using Schrodinger software to analyze the orientations, interactions and binding modes of these derivatives at the adenine -5-triphosphate binding site of EGFR (PDB ID: 2ITY), which indicated that the ligands show good interactions with active site residues in this structural benzothiazole class, and are considered lead compounds for further development as anti-breast cancer drugs

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Section: Antimicrobial Activitymentioning

confidence: 99%

“…24,25 ESI-MS was run negative mode using a ZQ-4000 single quadrupole mass spectrometer. [26][27][28][29][30][31] For 1 H-NMR 13 C-NMR (126MHz), CDCl 3 , spectroscopy, Bruker Advance 500 MHz equipment was employed, and chemical shifts were recorded in ppm.…”

Section: Chemistrymentioning

confidence: 99%

Synthesis, Characterisation, Molecular Docking Studies and Biological Evaluation of Novel Benzothiazole Derivatives as EGFR Inhibitors for Anti-breast Cancer Agents

Priya M,

Devhare,

Dharmamoorthy

et al. 2023

IJPQA

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“…5 Given their fascinating biological significance, the assembly of these important six-membered N , S -containing heterocycles has been widely studied. General methods including the cyclization reactions of thioureas with 3-halopropionic acid derivatives, 6 cyclopropenones 7 or acryloyl acid derivatives 8 and the condensation reactions between amines and α,β-unsaturated acyl isothiocyanates 9 (Scheme 2a). Alternative synthetic pathways have been widely applied in the synthesis of polycyclic fused 2-imino-1,3-thiazinones.…”

Section: Introductionmentioning

confidence: 99%

Lewis base-catalyzed cascade [4 + 2]-annulation reaction of N-alkoxy acrylamides and acyl isothiocyanates: facile access to 2-imino-1,3-thiazinone derivatives

Wang,

Tian,

Shi

et al. 2023

Org. Biomol. Chem.

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Pyridine‐2,6‐Dicarboxamide Proligands and their Cu(II)/Zn(II) Complexes Targeting Staphylococcus Aureus for the Attenuation of In Vivo Dental Biofilm

Chaudhary,

Agrahari,

Biswas

et al. 2024

Adv Healthcare Materials

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In the pursuit to combat stubborn bacterial infections, particularly those stemming from gram‐positive bacteria, our study is an attempt to craft a precision‐driven platform characterized by unparalleled selectivity, specificity, and synergistic antimicrobial mechanisms. Leveraging remarkable potential of metalloantibiotics in antimicrobial applications, herein, we rationally design, synthesize, and characterize a new library of Pyridine‐2,6‐dicarboxamide ligands and their corresponding transition metal Cu(II)/Zn(II) complexes. The lead compound L11 demonstrate robust antibacterial properties against Staphylococcus aureus (MIC = 2‐16 µg/mL), methicillin and vancomycin‐resistant S. aureus (MIC = 2‐4 µg/mL) and exhibit superior antibacterial activity when compared to FDA‐approved vancomycin, the drug of last resort. Additionally, the compound exhibited notable antimicrobial efficacy against resistant enterococcus strains (MIC = 2‐8 µg/mL). To unravel mechanistic profile, advanced imaging techniques including SEM and AFM were harnessed, collectively suggesting a mechanistic pathway involving cell wall disruption. Live/dead fluorescence studies further confirm efficacy of L11 and its complexes against S. aureus membranes. Our translational exploration extends to a rat model, indicating promising In‐vivo therapeutic potential. Thus, our comprehensive research initiative has capabilities to transcends the confines of our laboratory, heralding a pivotal step toward combatting antibiotic‐resistant pathogens and advancing the frontiers of metalloantibiotics based therapy with a profound clinical implication.This article is protected by copyright. All rights reserved

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Novel quinoline/thiazinan-4-one hybrids; design, synthesis, and molecular docking studies as potential anti-bacterial candidates against MRSA

Abstract: In an attempt to develop effective and safe antibacterial agents, thiazinanones bearing the quinolone scaffold were prepared by reaction of the corresponding (quinolinylmethylene)hydrazinecarbothioamides with 2,3-diphenylcycloprop-2-enone.

Cited by 6 publications

References 47 publications

Synthesis, Characterisation, Molecular Docking Studies and Biological Evaluation of Novel Benzothiazole Derivatives as EGFR Inhibitors for Anti-breast Cancer Agents

Synthesis, Characterisation, Molecular Docking Studies and Biological Evaluation of Novel Benzothiazole Derivatives as EGFR Inhibitors for Anti-breast Cancer Agents

Lewis base-catalyzed cascade [4 + 2]-annulation reaction of N-alkoxy acrylamides and acyl isothiocyanates: facile access to 2-imino-1,3-thiazinone derivatives

Pyridine‐2,6‐Dicarboxamide Proligands and their Cu(II)/Zn(II) Complexes Targeting Staphylococcus Aureus for the Attenuation of In Vivo Dental Biofilm

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