Synthesis, crystal structures and antimicrobial activities of 3-methyl and 3-bromo substituted benzo[b]thiophene based thiosemicarbazones

Öztürk E., SUBAŞI E., Çakmakçı E. S., Şahiner A., ŞEN YÜKSEL B.

Journal of Sulfur Chemistry, cilt.45, sa.1, ss.101-119, 2023 (SCI-Expanded) identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 45 Sayı: 1
  • Basım Tarihi: 2023
  • Doi Numarası: 10.1080/17415993.2023.2260916
  • Dergi Adı: Journal of Sulfur Chemistry
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus, Academic Search Premier, Chemical Abstracts Core, Chimica
  • Sayfa Sayıları: ss.101-119
  • Anahtar Kelimeler: antifungal activity, antimicrobial activity, Benzothiophene, crystal structure, thiosemicarbazone
  • Dokuz Eylül Üniversitesi Adresli: Evet

Özet

A series of thiosemicarbazones (TSCs) (L1–5) containing benzothiophen moiety were prepared via the reaction of 3-methyl/3-bromobenzo[b]thiophene-2-carboxaldehyde with appropriate thiosemicarbazides. The compounds were confirmed by elemental analysis, FT-IR, 1H NMR, MALDI-TOF and single crystal X-Ray diffraction techniques. The compounds exist in the E conformation with respect to the azomethine C = N double bond as confirmed by their C8/C9/N1/N2 torsion angles being 178.4(2)° (L1),–175.2(5)/177.4(5)° (L2), 177.5(2)° (L3), 179.7(3)° (L4), and–177.4(7)° (L5). These compounds were researched for their antibacterial activity against Gram-positive bacteria (E. faecalis and S. aureus), Gram-negative bacteria (E. coli, P. aeruginosa and S. marcescens) and antifungal activity against a yeast species C. albicans. The ligands possessed varying degrees of antimicrobial activity. Generally, the compounds demonstrated higher efficacy against gram-positive bacteria than gram-negative ones. The antifungal activity of the compounds against C. albicans was found to be lower in comparison to their activity against bacteria.