Synthesis of Novel Dihydropyrazolo[1,5-C]pyrimidin-7(3h)-One/-Thione Derivatives

Önal, Zülbiye; Ceran, Hacer; Şahin, Eda

doi:10.1515/hc.2008.14.4.245

Cited by 4 publications

(3 citation statements)

References 12 publications

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“…Schiff bases, having been found by Hugo Schiff in 1864, are ketone or aldehyde like groups with an imine (−C=N−) structure instead of the carbonyl group, and have become the focus of attention due to their various biological activities, such as analgesic, antibacterial, antioxidant, antimalarial, anti‐cancer, anti‐fungal, anti‐helminthic, antitubercular, antidiabetic, anti‐viral, and anti‐dyslipidemia [3] . In recent years, the reactions of aminopyrimidine‐2‐one/thione derivatives with isothiocyanate, [4] 1,3‐dicarbonyl compounds, [5] aryl chlorides, [6] various Schiff bases and transition metal complexes [7] have been reported. Nowadays, theoretical, and experimental comparison of N‐aminopyrimidine‐2‐one derivatives have become popular [4b,8] …”

Section: Introductionmentioning

confidence: 99%

Design, Synthesis, Cytotoxic Activity, and In Silico Studies of New Schiff Bases Including Pyrimidine Core

Karatas¹,

Ridler²,

Türkmenoğlu³

et al. 2023

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In here, two new Schiff base molecules (3 and 4) were synthesized from the condensation reaction of 1-amino-5benzoyl-4-phenylpyrimidine-2(1H)-one (1) and 1-amino-5-(4methylbenzoyl)-4-p-tolylpyrimidin-2(1H)-one (2) with 4-bromobenzaldehyde. These molecules were completely characterized by IR, NMR, and HR-MS. Moreover, molecule 4 was determined by single crystal x-ray diffraction (SC-XRD) patterns. The crystallographic analysis revealed that molecule 4 crystallizes in the monoclinic system, space group P2 1 /c. The molecules were screened in colon, lung and liver cell lines. The results showed that molecule 4 had cytotoxic activity in all screened cancer cell lines. Molecular docking studies of molecules 3 and 4, which were synthesized experimentally and whose cytotoxic activities were examined, were carried out with in silico approaches. Binding parameter values and active binding sites were determined by interacting the compounds with EGFR (PDB ID : 1M17) and VEGFR-2 (PDB ID : 4ASD) crystal structures, respectively, in molecular docking. In addition, the theoretical pharmacokinetic properties of compounds 3 and 4 were evaluated using ADME analysis.

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Section: Introductionmentioning

confidence: 99%

Design, Synthesis, Cytotoxic Activity, and In Silico Studies of New Schiff Bases Including Pyrimidine Core

Karatas¹,

Ridler²,

Türkmenoğlu³

et al. 2023

ChemistrySelect

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“…Aminopyrimidine-2-one/thione derivatives appeared to be an important starting compound in synthetic organic chemistry. In recent years, the reactions of aminopyrimidine-2one/thione derivatives with isothiocyanate [14,15], 1,3-dicarbonyl compounds [16], aryl chlorides [17] and transition metal complexes [18,19] have been reported. Nowadays, theoretical, and experimental comparison of N-aminopyrimidine-2-one derivatives have become popular [15,20,21].…”

Section: Introductionmentioning

confidence: 99%

A New Schiff Base Molecule Prepared from Pyrimidine-2-thione: Synthesis, Spectral Characterization, Cytotoxic Activity, DFT, and Molecular Docking Studies

Kökbudak¹,

Türkmenoğlu²,

Akkoç³

2022

Adıyaman University Journal of Science

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Schiff base derivatives are some of the most widely used organic compounds for industrial purposes and they exhibit a broad range of biological activities. In this paper, a new Schiff base derivative (2) synthesized from the condensation reaction of 1-amino-5-benzoyl)-4phenylpyrimidine-2(1H)-thione (1) with 2-chlorobenzaldehyde. The new compound was characterized by 1 H, 13 C NMR, and FT-IR. The biological activity property of this compound was tested against two different cancer cell lines and a healthy human cell line. The results demonstrate that molecule 2 has antiproliferative activity. In molecular modeling studies, the interaction site was examined using the epidermal growth factor receptor (EGFR) tyrosine kinase domain. Alignment in molecular docking, surface mapping binding, amino acids, and binding energy calculated. Glide score energy was found to be -9.820 kcal/mol and it predicted that the bonding interaction is strong. Theoretical calculations were made to compare the experimental and theoretical data. These calculations were performed on the 6-31 G* basis set using the Density Functional Theory (DFT) method and Becke-3-Parameter-Lee-Yang-Parr (B3LYP).

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“…Also conformational analysis and quantum chemical calculations were carried out by means of MMP2, CNDO, MNDO and AM1 approximation methods for a series of compounds which are functionalized pyrimidine derivatives 8,9 . The N-aminopyrimidine derivatives 1a-f which exhibit a free N-NH 2 derivatives 1a-f with several anhydrides, isocyanates, isothiocyanates and 1,3-dicarbonyl compounds have been reported in different solvents at various temperatures [12][13][14][15][16][17] .…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Characterization of Diazenyl-1,3-diphenylpropane-1,3-dione and 5-[Hydroxy(phenyl)methyl]-4-phenylpyrimidine Derivatives

Önal¹,

Özalp²,

Aslan³

2014

Asian J. Chem.

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Various novel diazenyl-1,3-diphenylpropane-1,3-dione derivatives (2a-f) were prepared by the condensation of the diazonium salts of N-aminopyrimidine derivatives with β-diketones. Also, a series of novel 5-[hydroxy(phenyl)methyl]-4-phenylpyrimidine derivatives (3a-f) were synthesized from the reduction reactions of N-aminopyrimidine derivatives with NaBH4. The structures of all the new synthesized compounds were characterized by the 13 C-NMR, 1 H-NMR and IR spectroscopic data and elemental analysis.

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Synthesis of Novel Dihydropyrazolo[1,5-C]pyrimidin-7(3h)-One/-Thione Derivatives

Cited by 4 publications

References 12 publications

Design, Synthesis, Cytotoxic Activity, and In Silico Studies of New Schiff Bases Including Pyrimidine Core

Design, Synthesis, Cytotoxic Activity, and In Silico Studies of New Schiff Bases Including Pyrimidine Core

A New Schiff Base Molecule Prepared from Pyrimidine-2-thione: Synthesis, Spectral Characterization, Cytotoxic Activity, DFT, and Molecular Docking Studies

Synthesis and Characterization of Diazenyl-1,3-diphenylpropane-1,3-dione and 5-[Hydroxy(phenyl)methyl]-4-phenylpyrimidine Derivatives

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