Design, synthesis, in vitro antiproliferative activity properties, quantum chemical and molecular docking studies of novel Schiff bases incorporating pyrimidine nucleus

Devim, Mahmut; Akkoç, Senem; Zeyrek, Celal Tuğrul; Aslan, Halime Güzin; Kökbudak, Zülbiye

doi:10.1016/j.molstruc.2022.132421

Cited by 10 publications

(3 citation statements)

References 27 publications

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“…They found that some of the compounds exhibited higher cytotoxic activity against MGC‐803 compared to 5‐fluorouracil (5‐Fu), which is a positive control drug. Devim and coworkers synthesized a series of molecules incorporating pyrimidine core and tested their cytotoxic activities against human breast adenocarcinoma cell line (MDA‐MB‐231) and DLD‐1 for 48 h [1a] . They found that these molecules have antiproliferative activities, with IC 50 values ranging from 58.59 μM to >200 μM for MDA‐MB‐231 and ranging from 118.90 μM to >200 μM for DLD‐1.…”

Section: Resultsmentioning

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: Resultsmentioning

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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“…1. [28][29][30] Indeno[1,2-b]quinoxaline skeleton exist in a large number of drug candidates (Fig. 1).…”

Section: Introductionmentioning

confidence: 99%

New multicomponent reactions in water: a facile synthesis of 1,3-dioxo-2-indanilidene-heterocyclic scaffolds and indenoquinoxalines through reaction of ninhydrin-malononitrile adduct with diverse N-binucleophiles

2022

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“…The compound, namely 1-(2,4dichlorobenzylideneamino)-5-benzoyl-4-phenylpyrimidin-2(1H)-one, demonstrated higher toxic effect on colon cancer cells in comparison to cisplatin, with an IC50 value of 34.41 μM. In a conducted study by Devim and coworkers, similar pyrimidine-based compounds were developed and screened against breast and colon cancer cell lines for 48 h[53]. They found that the IC50 values of the molecules ranged from 118.90 μM to ˃200 μM in the DLD-1 cell line.…”

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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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Design, synthesis, in vitro antiproliferative activity properties, quantum chemical and molecular docking studies of novel Schiff bases incorporating pyrimidine nucleus

Cited by 10 publications

References 27 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

New multicomponent reactions in water: a facile synthesis of 1,3-dioxo-2-indanilidene-heterocyclic scaffolds and indenoquinoxalines through reaction of ninhydrin-malononitrile adduct with diverse N-binucleophiles

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

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