TY  - JOUR
AU  - Doğan, Şengül Dilem
AU  - Özcan, Esma
AU  - Çetinkaya, Yasin
AU  - İhsan Han, Muhammed
AU  - Şahin, Onur
AU  - Bogojević Škaro, Sanja
AU  - Nikodinović-Runić, Jasmina
AU  - Gündüz, Miyase Gözde
PY  - 2023
UR  - https://www.sciencedirect.com/science/article/pii/S0022286023012486
UR  - https://imagine.imgge.bg.ac.rs/handle/123456789/1935
AB  - In the present work, we report the synthesis, structural characterization, and computational studies of (E)-N'-((5-nitrofuran-2-yl)methylene)quinoline-8-sulfonohydrazide (QNF) as a potential antimicrobial drug candidate. To design the target molecule, we utilized a molecular hybridization technique that connects two antimicrobial pharmacophores (quinoline and 5-nitrofuran rings) with a sulfonyl hydrazone moiety. QNF was synthesized by the condensation of quinoline-8-sulfonohydrazide with 5-nitrofuran-2-carbaldehyde, and characterized by various spectral techniques including single-crystal X-ray crystallography. QNF was extensively evaluated for its antibacterial and antifungal activity. The inhibition capacity of QNF on Candida albicans filamentation and biofilm formation was further investigated. Biofilm inhibition of QNF against C. albicans was supported by molecular docking studies in the binding site of agglutinin-like sequence 3 (Als3). Drug-like profile of QNF was confirmed by in silico calculation of its significant physicochemical properties. Additionally, the optimized geometrical structure, natural bond orbital calculations, frontier molecular orbital and molecular electrostatic potential analysis of QNF were carried out using the density functional theory method at the B3LYP with 6-31+G(d,p) basis set. 1H and 13C NMR chemical shift values were performed using the gauge-invariant atomic orbital method. Structural parameters and NMR values obtained experimentally were compared with the calculated values.
T2  - Journal of Molecular Structure
T1  - Linking quinoline ring to 5-nitrofuran moiety via sulfonyl hydrazone bridge: Synthesis, structural characterization, DFT studies, and evaluation of antibacterial and antifungal activity
SP  - 136155
VL  - 1292
DO  - 10.1016/j.molstruc.2023.136155
ER  - 

@article{
author = "Doğan, Şengül Dilem and Özcan, Esma and Çetinkaya, Yasin and İhsan Han, Muhammed and Şahin, Onur and Bogojević Škaro, Sanja and Nikodinović-Runić, Jasmina and Gündüz, Miyase Gözde",
year = "2023",
abstract = "In the present work, we report the synthesis, structural characterization, and computational studies of (E)-N'-((5-nitrofuran-2-yl)methylene)quinoline-8-sulfonohydrazide (QNF) as a potential antimicrobial drug candidate. To design the target molecule, we utilized a molecular hybridization technique that connects two antimicrobial pharmacophores (quinoline and 5-nitrofuran rings) with a sulfonyl hydrazone moiety. QNF was synthesized by the condensation of quinoline-8-sulfonohydrazide with 5-nitrofuran-2-carbaldehyde, and characterized by various spectral techniques including single-crystal X-ray crystallography. QNF was extensively evaluated for its antibacterial and antifungal activity. The inhibition capacity of QNF on Candida albicans filamentation and biofilm formation was further investigated. Biofilm inhibition of QNF against C. albicans was supported by molecular docking studies in the binding site of agglutinin-like sequence 3 (Als3). Drug-like profile of QNF was confirmed by in silico calculation of its significant physicochemical properties. Additionally, the optimized geometrical structure, natural bond orbital calculations, frontier molecular orbital and molecular electrostatic potential analysis of QNF were carried out using the density functional theory method at the B3LYP with 6-31+G(d,p) basis set. 1H and 13C NMR chemical shift values were performed using the gauge-invariant atomic orbital method. Structural parameters and NMR values obtained experimentally were compared with the calculated values.",
journal = "Journal of Molecular Structure",
title = "Linking quinoline ring to 5-nitrofuran moiety via sulfonyl hydrazone bridge: Synthesis, structural characterization, DFT studies, and evaluation of antibacterial and antifungal activity",
pages = "136155",
volume = "1292",
doi = "10.1016/j.molstruc.2023.136155"
}

Doğan, Ş. D., Özcan, E., Çetinkaya, Y., İhsan Han, M., Şahin, O., Bogojević Škaro, S., Nikodinović-Runić, J.,& Gündüz, M. G.. (2023). Linking quinoline ring to 5-nitrofuran moiety via sulfonyl hydrazone bridge: Synthesis, structural characterization, DFT studies, and evaluation of antibacterial and antifungal activity. in Journal of Molecular Structure, 1292, 136155.
https://doi.org/10.1016/j.molstruc.2023.136155

Doğan ŞD, Özcan E, Çetinkaya Y, İhsan Han M, Şahin O, Bogojević Škaro S, Nikodinović-Runić J, Gündüz MG. Linking quinoline ring to 5-nitrofuran moiety via sulfonyl hydrazone bridge: Synthesis, structural characterization, DFT studies, and evaluation of antibacterial and antifungal activity. in Journal of Molecular Structure. 2023;1292:136155.
doi:10.1016/j.molstruc.2023.136155 .

Doğan, Şengül Dilem, Özcan, Esma, Çetinkaya, Yasin, İhsan Han, Muhammed, Şahin, Onur, Bogojević Škaro, Sanja, Nikodinović-Runić, Jasmina, Gündüz, Miyase Gözde, "Linking quinoline ring to 5-nitrofuran moiety via sulfonyl hydrazone bridge: Synthesis, structural characterization, DFT studies, and evaluation of antibacterial and antifungal activity" in Journal of Molecular Structure, 1292 (2023):136155,
https://doi.org/10.1016/j.molstruc.2023.136155 . .