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

Hafize Özcan*, Anıl Deliorman, Ömer Zaim, Nurcan Tüzün

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

Abstract

Four novel macrocyclic compounds with furan and thiophene were synthesized, characterized by IR, 1H NMR, 13C NMR, and Q-TOF spectral data. Antimicrobial activities of these compounds were tested against Gram− Escherichia coli ATCC 25922, Gram− E. coli O157 : H7ATCC 43895, Gram+ Staphylococcus aureus ATCC 25923, Gram− Listeria monocytogenes ATCC 19115, Gram− Salmonella typhimurium ATCC 14028 and Candida albicans 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 3-dimensional geometries and electronic properties.

Original languageEnglish
Article numbere202302095
JournalChemistrySelect
Volume8
Issue number27
DOIs
Publication statusPublished - 20 Jul 2023

Bibliographical note

Publisher Copyright:
© 2023 Wiley-VCH GmbH.

Funding

We gratefully acknowledge the financial support of scientific research project commission of Trakya University (TUBAP 2014/42). The authors gratefully acknowledge the National High Performance Computing Center at ITU (Grant Number: 1011382021) and TUBITAK ULAKBIM, High Performance and Grid Computing Center (TRUBA resources) for computational sources.

FundersFunder number
TUBITAK ULAKBIM
International Technological University1011382021
Trakya ÜniversitesiTUBAP 2014/42
Sheikh Bahaei National High Performance Computing Center, Isfahan University of Technology

    Keywords

    • antimicrobial
    • dome-shaped
    • furan
    • macrocyclic
    • thiophene

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