TY  - JOUR
AU  - Gunduz, Miyase Gozde
AU  - Dengiz, Cagatay
AU  - Aslan, Ebru Kocak
AU  - Škaro Bogojević, Sanja
AU  - Nikodinović-Runić, Jasmina
PY  - 2022
UR  - https://imagine.imgge.bg.ac.rs/handle/123456789/1529
AB  - In the present study, we designed three novel compounds via the combination of two precious nitrogencontaining scaffolds; 1,4-dihydropyridine (DHP) and azole, in the same molecule. To synthesize the title compounds, initially, azolyl benzaldehydes were obtained through the nucleophilic aromatic substitution reaction of 4-fluorobenzaldehyde with pyrazole, imidazole or 1,2,4-triazole. Subsequently, an unsymmetrical Hantzsch reaction was applied to achieve DHP scaffold, thus the target molecules. After structural characterization, the effects of various azole rings on optical and non-linear optical (NLO) properties were investigated by computational methods. Band gaps, chemical hardness/softness, dipole moments, average polarizability, first hyperpolarizability values were computed for the target compounds at the CAM-B3LYP/6-31++G(d,p) level of theory. The comparable results confirmed the potential of DHP-azole hybrids to be utilized in NLO devices. The title molecules were further tested for their antibacterial and antifungal activities following the evaluation of their drug likeness properties. The compounds containing imidazole or triazole rings represented better antifungal properties than antibacterial activities. Molecular docking studies were performed in the catalytic site of lanosterol 14 alpha-demethylase, CYP51, from Candida albicans to explain the obtained biological results and suggest molecular modifications to endow this class of molecules with improved antifungal effects.
PB  - Elsevier, Amsterdam
T2  - Journal of Molecular Structure
T1  - Attaching azoles to Hantzsch 1,4-dihydropyridines: Synthesis, theoretical investigation of nonlinear optical properties, antimicrobial evaluation and molecular docking studies
VL  - 1247
DO  - 10.1016/j.molstruc.2021.131316
ER  - 

@article{
author = "Gunduz, Miyase Gozde and Dengiz, Cagatay and Aslan, Ebru Kocak and Škaro Bogojević, Sanja and Nikodinović-Runić, Jasmina",
year = "2022",
abstract = "In the present study, we designed three novel compounds via the combination of two precious nitrogencontaining scaffolds; 1,4-dihydropyridine (DHP) and azole, in the same molecule. To synthesize the title compounds, initially, azolyl benzaldehydes were obtained through the nucleophilic aromatic substitution reaction of 4-fluorobenzaldehyde with pyrazole, imidazole or 1,2,4-triazole. Subsequently, an unsymmetrical Hantzsch reaction was applied to achieve DHP scaffold, thus the target molecules. After structural characterization, the effects of various azole rings on optical and non-linear optical (NLO) properties were investigated by computational methods. Band gaps, chemical hardness/softness, dipole moments, average polarizability, first hyperpolarizability values were computed for the target compounds at the CAM-B3LYP/6-31++G(d,p) level of theory. The comparable results confirmed the potential of DHP-azole hybrids to be utilized in NLO devices. The title molecules were further tested for their antibacterial and antifungal activities following the evaluation of their drug likeness properties. The compounds containing imidazole or triazole rings represented better antifungal properties than antibacterial activities. Molecular docking studies were performed in the catalytic site of lanosterol 14 alpha-demethylase, CYP51, from Candida albicans to explain the obtained biological results and suggest molecular modifications to endow this class of molecules with improved antifungal effects.",
publisher = "Elsevier, Amsterdam",
journal = "Journal of Molecular Structure",
title = "Attaching azoles to Hantzsch 1,4-dihydropyridines: Synthesis, theoretical investigation of nonlinear optical properties, antimicrobial evaluation and molecular docking studies",
volume = "1247",
doi = "10.1016/j.molstruc.2021.131316"
}

Gunduz, M. G., Dengiz, C., Aslan, E. K., Škaro Bogojević, S.,& Nikodinović-Runić, J.. (2022). Attaching azoles to Hantzsch 1,4-dihydropyridines: Synthesis, theoretical investigation of nonlinear optical properties, antimicrobial evaluation and molecular docking studies. in Journal of Molecular Structure
Elsevier, Amsterdam., 1247.
https://doi.org/10.1016/j.molstruc.2021.131316

Gunduz MG, Dengiz C, Aslan EK, Škaro Bogojević S, Nikodinović-Runić J. Attaching azoles to Hantzsch 1,4-dihydropyridines: Synthesis, theoretical investigation of nonlinear optical properties, antimicrobial evaluation and molecular docking studies. in Journal of Molecular Structure. 2022;1247.
doi:10.1016/j.molstruc.2021.131316 .

Gunduz, Miyase Gozde, Dengiz, Cagatay, Aslan, Ebru Kocak, Škaro Bogojević, Sanja, Nikodinović-Runić, Jasmina, "Attaching azoles to Hantzsch 1,4-dihydropyridines: Synthesis, theoretical investigation of nonlinear optical properties, antimicrobial evaluation and molecular docking studies" in Journal of Molecular Structure, 1247 (2022),
https://doi.org/10.1016/j.molstruc.2021.131316 . .