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

• Published in: Russian Journal of Physical Chemistry A Vol. 97; no. 11; pp. 2488 - 2500
• Main Authors: Ustabaş, Reşat, Süleymanoğlu, Nevin, Çelik, Fatih, Güler, Halil İbrahim, Bektaş, Kadriye İnan, Direkel, Şahin, Ünver, Yasemin
• Format: Journal Article
• Language: English
• Published: Moscow Pleiades Publishing 01.11.2023; Springer Nature B.V
• Subjects: Butanol; Chemistry; Chemistry and Materials Science; In vitro methods and tests; Low concentrations; Microorganisms; NMR; Nuclear magnetic resonance; Physical Chemistry; Structure of Matter and Quantum Chemistry; Schiff base; DFT study; antibacterial; thiophene; leishmanicidal activity and in silico study
• ISSN: 0036-0244; 1531-863X
• DOI: 10.1134/S0036024423110274

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.