Attaching azoles to Hantzsch 1,4-dihydropyridines: Synthesis, theoretical investigation of nonlinear optical properties, antimicrobial evaluation and molecular docking studies
Samo za registrovane korisnike
2022
Autori
Gunduz, Miyase GozdeDengiz, Cagatay
Aslan, Ebru Kocak
Škaro Bogojević, Sanja
Nikodinović-Runić, Jasmina
Članak u časopisu (Objavljena verzija)
Metapodaci
Prikaz svih podataka o dokumentuApstrakt
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.
Ključne reči:
Nonlinear optics / Molecular hybridization / Hantzsch reaction / Donor-acceptor / Charge-transfer / AntifungalIzvor:
Journal of Molecular Structure, 2022, 1247Izdavač:
- Elsevier, Amsterdam
Finansiranje / projekti:
- BAGEP Award of the Science Academy
DOI: 10.1016/j.molstruc.2021.131316
ISSN: 0022-2860
WoS: 000709577800009
Scopus: 2-s2.0-85113798469
Institucija/grupa
Institut za molekularnu genetiku i genetičko inženjerstvoTY - 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 . .