New Thiophene–Butanol Derivatives: Synthesis, Spectroscopic Characterization, DFT, Biological Activities and In Silico Study

USTABAŞ R., SÜLEYMANOĞLU N., ÇELİK F., GÜLER H. İ., Bektaş K. İ., Direkel Ş., ...More

Russian Journal of Physical Chemistry A, vol.97, no.11, pp.2488-2500, 2023 (SCI-Expanded) identifier identifier

  • Publication Type: Article / Article
  • Volume: 97 Issue: 11
  • Publication Date: 2023
  • Doi Number: 10.1134/s0036024423110274
  • Journal Name: Russian Journal of Physical Chemistry A
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus, Aquatic Science & Fisheries Abstracts (ASFA), Chemical Abstracts Core, Compendex
  • Page Numbers: pp.2488-2500
  • Keywords: antibacterial, DFT study, leishmanicidal activity and in silico study, Schiff base, thiophene
  • Karadeniz Technical University Affiliated: Yes

Abstract

Abstract: In this study, 3-methyl/5-bromo/5-nitro-thiophene-2-carbaldehydes were reacted with 4‑amino-1-propanol and thiophene derivatives including alcohole group (1–3) were obtained. The newly compounds (1–3) were characterized by FTIR and NMR methods. The optimized geometries, NMR-IR data and MEP map of compounds 1–3 were obtained at DFT/B3LYP/6-311++G(d,p) level. The leishmanicidal activity against Leishmania infantum promastigotes was determined in vitro by microdilution broth method for compounds 1–3. As a result, compounds 1–3 studied were effective against Leishmania specie, while compound 3 was found to be effective at very low concentrations. In addition, compounds 1–3 were tested for their antimicrobial activity. 8 different pathogenic microorganisms were selected for the antimicrobial activity test. The compounds 1–3 showed antimicrobial activities, but compound 3 demonstrated excellent antimicrobial activities against all the tested microorganisms. To examine possible interactions between synthesized compound 3 and target proteins was used by in silico analysis.