Synthesis, Antimicrobial Evaluation, DFT, in Silico‐Docking, and ADMET Investigations of Novel Chromene‐Based 2,4‐Thiazolidinediones

Three series of thiazolidinedione (TZD) derivatives (5a‐f, 7a‐f, and 9a‐f) were prepared efficiently. Afterward, the synthesized candidates’ antibacterial efficacy against both gram‐positive and gram‐negative bacteria was assessed. Compounds 7c, 7d, and 7f had values comparable to that of ampicillin...

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Bibliographic Details
Published in:Chemistry & biodiversity 2024-10, Vol.21 (10), p.e202401095-n/a
Main Authors: Mohamed Ahmed, Mohamed S., Alfraiji, Redhab AJ, Attaby, Fawzy A., Abdallah, Zeinab A.
Format: Article
Language:English
Subjects:
2,4-Thiazolidinedione
ADMET
Ampicillin
Anti-Bacterial Agents - chemical synthesis
Anti-Bacterial Agents - chemistry
Anti-Bacterial Agents - pharmacology
Antiinfectives and antibacterials
Antimicrobial
Bacteria
Benzopyrans - chemical synthesis
Benzopyrans - chemistry
Benzopyrans - pharmacology
Chemical synthesis
Chromene
Density Functional Theory
DFT
Gram-negative bacteria
Gram-Negative Bacteria - drug effects
Gram-Positive Bacteria - drug effects
In silico-docking
Microbial Sensitivity Tests
Molecular Docking Simulation
Molecular Structure
Staphylococcus aureus - drug effects
Structure-Activity Relationship
Thiazolidinediones
Thiazolidinediones - chemical synthesis
Thiazolidinediones - chemistry
Thiazolidinediones - metabolism
Thiazolidinediones - pharmacology
Toxicity
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Summary:Three series of thiazolidinedione (TZD) derivatives (5a‐f, 7a‐f, and 9a‐f) were prepared efficiently. Afterward, the synthesized candidates’ antibacterial efficacy against both gram‐positive and gram‐negative bacteria was assessed. Compounds 7c, 7d, and 7f had values comparable to that of ampicillin, a reference antibiotic, whereas compounds 5c, 5d, and 7e exhibited the greatest values (23.0±1.0, 27.7±0.6, and 20.0±1.0, respectively) against gram‐positive bacteria (Staphylococcus aureus). The optimal structure of the produced molecules was determined by DFT computing. To assess the binding energy and elucidate the interaction between the potential candidates and different proteins, in silico docking is employed. ADMET analysis to assess the synthesized compounds’ toxicity, metabolism, excretion, distribution, and absorption.
ISSN:1612-1872
1612-1880
1612-1880
DOI:10.1002/cbdv.202401095