Akademik Veri Yönetim Sistemi
Journal of the Turkish Chemical Society, Section A: Chemistry, cilt.12, sa.4, ss.197-206, 2025 (Scopus, TRDizin)
A new azo dye containing quinolone (QANB) was synthesized by the ring-opening of pyranoquinolone (PQ), which was obtained from N-ethyl aniline and diethyl malonate. Surprisingly, we determined that under strong base conditions, azo coupling occurred at the 8-position of the quinolone group rather than at the 3-position of the pyroquinolone ring. Structure of 3-[1-ethyl-4-hydroxy-8-(4-nitro-phenylazo)-2-oxo-1,2-dihydro-quinolin-3-yl]-3-hydroxy-acrylic acid (QANB) was elucidated by1H NMR,13C NMR,13C NMR DEPT,13C NMR APT, 2D NMR (1H-1H COSY and1H-13C HMQC) and HRMS Analyses. Moreover, we investigated the antimicrobial activity of QANB on eight different bacteria and two different yeasts. The disc diffusion method and the minimum inhibitory concentration value determination (MIC) were used for antimicrobial activity. QANB demonstrated broad-spectrum antibacterial activity against both Gram-positive and Gram-negative bacteria. However, it has effectively shown activity against Entereobacter aerogenes (E. aerogenes), which causes pneumonia, sepsis, urinary tract infections, and wound infections. QANB also showed significant activity against Candida albicans (C. albicans). The fact that QANB is much more effective against C. albicans than nystatin, which is widely used as an antifungal drug, supports the idea that this compound can be used as a potential antifungal drug.