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


ÖZCAN H., Deliorman A., ZAİM Ö., Tüzün N.

ChemistrySelect, cilt.8, sa.27, 2023 (SCI-Expanded, Scopus) identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 8 Sayı: 27
  • Basım Tarihi: 2023
  • Doi Numarası: 10.1002/slct.202302095
  • Dergi Adı: ChemistrySelect
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus, Academic Search Premier
  • Anahtar Kelimeler: antimicrobial, dome-shaped, furan, macrocyclic, thiophene
  • Trakya Üniversitesi Adresli: Evet

Özet

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.