Crystal Structure, Hirshfeld Surface Analysis, In-Silico and Antimycotic Investigations of Methyl 6-methyl-4-(4-nitrophenyl)-2-oxo-1,2-dihydropyrimidine-5-carboxylate

Huseynzada, Alakbar; Mori, Matteo; Meneghetti, Fiorella; Israyilova, Aygun; Güney, Elif; Sayın, Koray; Chiarelli, Laurent R.; Demiralp, Mustafa; Hasanova, Ulviyya; Abbasov, V. М.

doi:10.3390/cryst13010052

Cited by 3 publications

(4 citation statements)

References 71 publications

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“…The best binding energies of CuONPs with chitin deacetylase (CDA) of A. niger, topoisomerase IV (TopoIV) of E. coli and tyrosyl-tRNA synthetase (TyrRS) of S. aureus were −7.25, −7.14 and −7.89 kcal mol −1 , respectively. CDA, which regulates the production of chitosan by removing the acetic group of the chitin substrate, has been suggested as a fungicide target due to its support for virulence and immunological invasion in the fungal cell wall, especially for agricultural approaches [33,34]. In the analysis with AGFR, the binding site of CDA was found at 40.165, 44.564, and −7.430 for x-y-z, respectively.…”

Section: Molecular Docking Analysismentioning

confidence: 99%

Bio-capped multifunctional CuO nanoparticles via Knautia arvensis for dye removal, antibacterial and antifungal efficiency, and molecular docking

Sazak,

Attar,

Ari Yuka

et al. 2024

Mater. Res. Express

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Copper oxide nanoparticles (CuONPs) synthesized using Knautia arvensis flower extract in an environmentally friendly and one-step procedure were characterized by UV–vis, FT-IR, SEM and DLS. The in vitro antibacterial and antifungal activities of CuONPs were determined using E. coli, S. aureus and A. niger. In silico antibacterial and antifungal evaluation of CuONPs were performed by molecular docking analysis using chitin deacetylase of A. niger, topoisomerase IV of E. coli and tyrosyl-tRNA synthetase of S. aureus. The best binding energy was determined using these microbial targets in molecular docking analyses and the antimicrobial mechanisms between the microorganism and the CuONP were elucidated. The degradation potential of Remazol brilliant blue R (RBBR) and Napthol blue black (NBB) dyes in the presence of CuONPs were investigated. The peak obtained at 289 nm as a result of UV–vis analysis revealed the presence of CuONPs. The spherical morphology of CuONPs and the particle size varying between 88–289 nm were visualized by SEM. DLS analysis pointed out the mean diameter of CuONPs was 189 nm along with the PDI value of 0.324. The 600 and 595 cm−1 vibrations attained in the FT-IR spectroscopy showed the presence of CuONPs. In addition, the presence of phenolic compounds found in the plant extract responsible for bio-capping of copper ions into CuONPs were enlightened by the FT-IR analysis. Dye degradation activity of CuONPs was found as 69% and 71% using NBB and RBBR at 50 °C in 90 min, respectively. Antifungal and antibacterial interactions of CuONPs with chitin deacetylase of A. niger, topoisomerase IV of E. coli and tyrosyl-tRNA synthetase of S. aureus were analyzed in order to reveal the antimicrobial mechanisms of CuONPs and it was found that CuONPs demonstrate significant interactions with those proteins with binding energies −7.25, −7.14 and −7.89 kcal mol−1, respectively.

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Section: Molecular Docking Analysismentioning

confidence: 99%

Bio-capped multifunctional CuO nanoparticles via Knautia arvensis for dye removal, antibacterial and antifungal efficiency, and molecular docking

Sazak,

Attar,

Ari Yuka

et al. 2024

Mater. Res. Express

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“…252-254⁰C. 1 H NMR spectrum (Figure 1): (DMSO-d6, δ, ppm), 2.15 s (3H, CH 3 ), 3.39 s (3H, OCH 3 ), 3.72 s (6H, 2OCH 3 ), 3.75 s (3H, OCH 3 ), 5.74 s (1H, CH), 6.18 s (2H, 2C Ar H), 6.9 s (1H, NH), 8.95 s (1H, NH). 13 C NMR spectrum (Figure 2): (DMSO-d6, δ, ppm), 17.78 (CH 3 ), 45.03 (CH), 50.14 (OCH 3 ), 55.1 (OCH 3 ), 55.7 (2OCH 3 ), 91.08 (2C Ar H), 96.03 (C), 113.71 (C), 147.84 (C Ar ), 152.12 (C Ar ), 158.99 (2C Ar ), 159.91 (COO), 166.25 (CO).…”

Section: Synthesis Of Dihydropyrimidinesmentioning

confidence: 99%

“…212-214⁰C. 1 H NMR spectrum (Figure 4): (DMSO-d 6 , δ, ppm), 2.26 s (3H, CH 3 ), 3.54 s (3H, OCH 3 ), 5.21-5.22 d (1H, CH, J=3 Hz), 7.41-7.44 d (2H, 2CArH, J=9 Hz), 7.8-7.83 d (2H, 2CArH, J=9 Hz), 7.86 s (1H, NH), 9.34 s (1H, NH). 13 C NMR spectrum (Figure 5): (DMSO-d 6 , δ, ppm), 18…”

Section: Synthesis Of Dihydropyrimidinesmentioning

confidence: 99%

“…One-pot multicomponent reactions are a very effective synthetic technique and a flexible tool for building different classes of compounds with a broad range of applications. Because multicomponent reactions provide a synthetic chemist intrinsically substantial benefits over traditional linear-type synthesis, such as straightforward operation, simple starting ingredients, high product complexity, and enormous product variety, interest in them is rising [1][2][3][4]. A three-component one-pot Biginelli reaction is one of these kinds of reactions that was used in the synthesis of heterocycles.…”

Section: Introductionmentioning

confidence: 99%

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Graphene Oxide-Modified Dihydropyrimidines

Huseynzada,

Hasanova,

Gakhramanova

2023

AChJ

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This study is devoted to the synthesis of various ensembles on the basis of graphene oxide nanolayers and dihydropyrimidines and the investigation of their antimicrobial activity. The “building blocks” of ensembles, viz dihydropyrimidines were synthesized by the Biginelli reaction in the presence of low-toxic copper triflate under microwave conditions. The positive side of the reaction is the absence of any additional purification stage, formed after cooling the solution precipitate just washed with a few amount of distilled water. The structures of synthesized compounds were determined by 1H, 13C and dept135 NMR spectroscopy methods. The second component, viz graphene oxide nanolayers, was synthesized by a modified Hummer method. The modification of the method is caused by the increasing of the oxidizing agent (H2SO4+KMnO4) concentration, which allowed to receive purier nanolayers. The structure and morphology of nanolayers were investigated by SEM and XRD methods, according to which it was determined that the thickness of nanolayers is 1 nm. Subsequently, graphene oxide was modified with dihydropyrimidines. The synthesis of ensembles was performed by non-covalent coupling of dihydropyrimidines with graphene oxide nanolayers by sonication. In addition, the antimicrobial activity of ensembles against S. aureus, Ps. aeruginosa and E. coli was performed. Obtained during the analysis results were compared with the activity of pristine antibiotic ampicillin. It was found that the addition of graphene oxide nanolayers to the dihydropyrimidine molecule allowed to improve the antimicrobial activity of dihydropyrimidines

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Development of a Bentonite Nanoparticle-Based Transdermal Drug Delivery System for Burn Wound Infection Prevention

Aliyev,

Hasanova,

Israyilova

2024

J Inorg Organomet Polym

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Crystal Structure, Hirshfeld Surface Analysis, In-Silico and Antimycotic Investigations of Methyl 6-methyl-4-(4-nitrophenyl)-2-oxo-1,2-dihydropyrimidine-5-carboxylate

Cited by 3 publications

References 71 publications

Bio-capped multifunctional CuO nanoparticles via Knautia arvensis for dye removal, antibacterial and antifungal efficiency, and molecular docking

Bio-capped multifunctional CuO nanoparticles via Knautia arvensis for dye removal, antibacterial and antifungal efficiency, and molecular docking

Graphene Oxide-Modified Dihydropyrimidines

Development of a Bentonite Nanoparticle-Based Transdermal Drug Delivery System for Burn Wound Infection Prevention

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