Furan and Thiophene Based Cycloheterophane Esters and Thioesters: Synthesis, Antimicrobial Activities, and DFT Calculations

Özcan, Hafize; Deliorman, Anıl; Zaim, Ömer; Tüzün, Nurcan Ş.

doi:10.1002/slct.202302095

ChemistrySelect

2023

DOI: 10.1002/slct.202302095

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Furan and Thiophene Based Cycloheterophane Esters and Thioesters: Synthesis, Antimicrobial Activities, and DFT Calculations

Hafize Özcan

Anıl Deliorman

Ömer Zaim

et al.

Abstract: ATCC 10231. Macrocyclic thioesters were found more efficient against selected microorganisms than other compounds, especially the thioester with thiophene ring notably showed results as effective as reference antibiotic AMP (ampicillin) against Staphylococcus aureus bacteria. DFT calculations on synthesized macromolecules provided insights into their 3dimensional geometries and electronic properties.

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2024

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Synthesis of 2-Ethylhexyl 5-Bromothiophene-2-Carboxylates; Antibacterial Activities against Salmonella Typhi, Validation via Docking Studies, Pharmacokinetics, and Structural Features Determination through DFT

Nazeer,

Qamar,

Rasool

et al. 2024

Molecules

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A new class of thiophene-based molecules of 5-bromothiophene-2-carboxylic acid (1) have been synthesized in current research work. All analogs 4A–4G were synthesized with optimized conditions by coupling reactions of 2-ethylhexyl 5-bromothiophene-2-carboxylate (3) with various arylboronic acids. The results indicated that the majority of compounds showed promising effective in vitro antibacterial activity. Herein, 2-ethylhexyl-5-(p-tolyl)thiophene-2-carboxylate (4F), in particular among the synthesized analogs, showed outstanding antibacterial action (MIC value 3.125 mg/mL) against XDR Salmonella Typhi compared to ciprofloxacin and ceftriaxone. The intermolecular interaction was investigated by using a molecular docking study of thiophene derivatives 4A–4G against XDR S. Typhi. The values of the binding affinity of functionalized thiophene molecules and ciprofloxacin were compared against bacterial enzyme PDB ID: 5ztj. Therefore, 4F appears to be a promising antibacterial agent and showed the highest potential value. Density functional theory (DFT) calculations were executed to examine the electronic, structural, and spectroscopic features of the newly synthesized molecules 4A–4G.

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Synthesis of 2-Ethylhexyl 5-Bromothiophene-2-Carboxylates; Antibacterial Activities against Salmonella Typhi, Validation via Docking Studies, Pharmacokinetics, and Structural Features Determination through DFT

Nazeer,

Qamar,

Rasool

et al. 2024

Molecules

View full text Add to dashboard Cite

show abstract

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Furan and Thiophene Based Cycloheterophane Esters and Thioesters: Synthesis, Antimicrobial Activities, and DFT Calculations

Cited by 1 publication

References 39 publications

Synthesis of 2-Ethylhexyl 5-Bromothiophene-2-Carboxylates; Antibacterial Activities against Salmonella Typhi, Validation via Docking Studies, Pharmacokinetics, and Structural Features Determination through DFT

Synthesis of 2-Ethylhexyl 5-Bromothiophene-2-Carboxylates; Antibacterial Activities against Salmonella Typhi, Validation via Docking Studies, Pharmacokinetics, and Structural Features Determination through DFT

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