Spectroscopic, quantum chemical and molecular docking studies on 2,4-dimethoxy-1,3,5-triazine: a potent inhibitor of protein kinase CK2 for the development of breast cancer drug

Akram, Noreen; Mansha, Asim; Premkumar, R.; Benial, A. Milton Franklin; Asim, Sadia; Iqbal, Shahzad Zafar; Ali, Hafiz Saqib

doi:10.1080/08927022.2020.1822526

Cited by 17 publications

(4 citation statements)

References 65 publications

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“…Three doublets of doublets were experimentally observed at 8. 63 13 C NMR chemical shifts was achieved, validating the structural assignment for the compound (3) (Figure 3).…”

Section: C−n and C−c Vibrationssupporting

confidence: 66%

“…Notably, the lone pair LP2 on atom N-7 proved to be an efficient electron donor, participating in a remarkable hyperconjugative interaction with the π* bond in C-1_N-6 . Additionally, LP2 on atom S-22 also acted as an electron donor, engaging in hyperconjugative interactions with π* bonds in C-18_C-19 and C-20_C-21 . Furthermore, we observed that the delocalization of ED between occupied Lewis-type and previously unoccupied non-Lewis-type orbitals led to the stabilization of donor–acceptor interactions.…”

Section: Resultsmentioning

confidence: 74%

“…62 Additionally, LP2 on atom S-22 also acted as an electron donor, engaging in hyperconjugative interactions with π* bonds in C-18_C-19 and C-20_C-21. 63 Furthermore, we observed that the delocalization of ED between occupied Lewis-type and previously unoccupied non-Lewis-type orbitals led to the stabilization of donor−acceptor interactions. The molecule exhibited strong intramolecular hyperconjugative interactions, resulting in the stabilization of the ring systems.…”

Section: Mulliken Analysismentioning

confidence: 85%

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Synthesis, Characterizations, and Quantum Chemical Investigations on Imidazo[1,2-a]pyrimidine-Schiff Base Derivative: (E)-2-Phenyl-N-(thiophen-2-ylmethylene)imidazo[1,2-a]pyrimidin-3-amine

Azzouzi,

Azougagh,

Ouchaoui

et al. 2023

ACS Omega

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In this study, (E)-2-phenyl-N-(thiophen-2ylmethylene)imidazo[1,2-a]pyrimidin-3-amine (3) is synthesized, and detailed spectral characterizations using 1 H NMR, 13 C NMR, mass, and Fourier transform infrared (FT-IR) spectroscopy were performed. The optimized geometry was computed using the density functional theory method at the B3LYP/6-311++G(d,p) basis set. The theoretical FT-IR and NMR ( 1 H and 13 C) analysis are agreed to validate the structural assignment made for (3). Frontier molecular orbitals, molecular electrostatic potential, Mulliken atomic charge, electron localization function, localized orbital locator, natural bond orbital, nonlinear optical, Fukui functions, and quantum theory of atoms in molecules analyses are undertaken and meticulously interpreted, providing profound insights into the molecular nature and behaviors. In addition, ADMET and drug-likeness studies were carried out and investigated. Furthermore, molecular docking and molecular dynamics simulations have been studied, indicating that this is an ideal molecule to develop as a potential vascular endothelial growth factor receptor-2 inhibitor.

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“…Three doublets of doublets were experimentally observed at 8. 63 13 C NMR chemical shifts was achieved, validating the structural assignment for the compound (3) (Figure 3).…”

Section: C−n and C−c Vibrationssupporting

confidence: 66%

Section: Resultsmentioning

confidence: 74%

Section: Mulliken Analysismentioning

confidence: 85%

See 1 more Smart Citation

Synthesis, Characterizations, and Quantum Chemical Investigations on Imidazo[1,2-a]pyrimidine-Schiff Base Derivative: (E)-2-Phenyl-N-(thiophen-2-ylmethylene)imidazo[1,2-a]pyrimidin-3-amine

Azzouzi,

Azougagh,

Ouchaoui

et al. 2023

ACS Omega

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“…The blue side of the molecule cognates to nucleophilic reactivity [ 38 , 39 ]. Hence, MEP mapping illustrated negative and positive sides of the molecule and indicated the tendency of the molecule to develop different interactions under the enzyme cavity [ 40 ].…”

Section: Resultsmentioning

confidence: 99%

A Combined Experimental and Computational Study of Novel Benzotriazinone Carboxamides as Alpha-Glucosidase Inhibitors

Khalid,

Shafqat,

Ahmad

et al. 2023

Molecules

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Diabetes is a chronic metabolic disorder of the endocrine system characterized by persistent hyperglycemia appears due to the deficiency or ineffective use of insulin. The glucose level of diabetic patients increases after every meal and medically recommended drugs are used to control hyperglycemia. Alpha-glucosidase inhibitors are used as antidiabetic medicine to delay the hydrolysis of complex carbohydrates. Acarbose, miglitol, and voglibose are commercial drugs but patients suffer side effects of flatulence, bloating, diarrhea, and loss of hunger. To explore a new antidiabetic drug, a series of benzotriazinone carboxamides was synthesized and their alpha-glucosidase inhibition potentials were measured using in vitro experiments. The compounds 14k and 14l were found to be strong inhibitors compared to the standard drug acarbose with IC50 values of 27.13 ± 0.12 and 32.14 ± 0.11 μM, respectively. In silico study of 14k and 14l was carried out using molecular docking to identify the type of interactions developed between these compounds and enzyme sites. Both potent compounds 14k and 14l exhibited effective docking scores by making their interactions with selected amino acid residues. Chemical hardness and orbital energy gap values were investigated using DFT studies and results depicted affinity of 14k and 14l towards biological molecules. All computational findings were found to be in good agreement with in vitro results.

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Synergistic Antimicrobial and Photocatalytic Properties of PVP-Ag-PEG Nanocomposites for Sustainable Leachate Treatment

Smonia Joe Princy,

Hentry,

Alharbi

et al. 2024

J Inorg Organomet Polym

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Spectroscopic, quantum chemical and molecular docking studies on 2,4-dimethoxy-1,3,5-triazine: a potent inhibitor of protein kinase CK2 for the development of breast cancer drug

Cited by 17 publications

References 65 publications

Synthesis, Characterizations, and Quantum Chemical Investigations on Imidazo[1,2-a]pyrimidine-Schiff Base Derivative: (E)-2-Phenyl-N-(thiophen-2-ylmethylene)imidazo[1,2-a]pyrimidin-3-amine

Synthesis, Characterizations, and Quantum Chemical Investigations on Imidazo[1,2-a]pyrimidine-Schiff Base Derivative: (E)-2-Phenyl-N-(thiophen-2-ylmethylene)imidazo[1,2-a]pyrimidin-3-amine

A Combined Experimental and Computational Study of Novel Benzotriazinone Carboxamides as Alpha-Glucosidase Inhibitors

Synergistic Antimicrobial and Photocatalytic Properties of PVP-Ag-PEG Nanocomposites for Sustainable Leachate Treatment

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