Synthesis of some new 2-(substitutedphenyl)imidazo[4,5-c] pyridine derivatives and their pharmacological properties

---

Tezin Türü: Yüksek Lisans

Tezin Yürütüldüğü Kurum: Ankara Üniversitesi, Eczacılık Fakültesi, Eczacılık Meslek Bilimleri Bölümü, Türkiye

Tezin Onay Tarihi: 2021

Tezin Dili: İngilizce

Öğrenci: MOFTAH ALTAIB MOFTAH ALSHALWI

Danışman: Ali Hakan Göker

Özet:

In the present study, required 5H-imidazo[4,5-c]pyridines  analogues (1a–1h) were prepared by the reaction of 3,4-diaminopyridine and sodium metabisulfite adduct of corresponding benzaldehydes (a1-a8).   Alkylation of 1a – 1h with 4-chlorobenzyl and /or butyl bromides under basic conditions (K₂CO₃, DMF) were formed as mainly N⁵ regioisomer (2a-2l).

 

The structure elucidation of the synthesized compounds was achieved by their ¹H-NMR, ¹³C-NMR, 2D-NOESY, 2D-COSY spectra and, Mass (ESI+) findings. The N⁵-regioisomeric structures were assigned with their 2D-NOESY spectra. 

 

Antibacterial activities of synthesized 20 compounds (1a-1h) and (2a-2l) against E. coli (ATCC 25922), P. aeruginosa (ATCC 27853), S. aureus (ATCC 29213), Methicillin resistant S. aureus (ATCC 43300) and, E.  faecalis (ATCC 29212) were evaluated as in vitro.  Among the synthesized compounds best activities were obtained with compounds 2g and 2h (IC₅₀ = 12.5 and 6.25 µg/mL, respectively) against E. faecalis. The compounds 1h, 2i, 2j, 2k, 2l showed moderate activity. There was no inhibitory effect against E. coli and P. aeruginosa.