Spectroscopic and electronic structure calculation of a potential chemotherapeutic agent 5-propyl-6-(p-tolylsulfanyl)pyrimidine-2,4(1H,3H)-dione using first principles

Al-Alshaikh, Monirah A.; Al‐Deeb, Omar A.; Alzoman, Nourah Z.; El-Emam, Ali A.; Srivastava, Richa; Sachan, Alok K.; Prasad, Onkar; Sinha, Leena

doi:10.1016/j.molstruc.2015.07.042

Cited by 6 publications

(2 citation statements)

References 82 publications

(56 reference statements)

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“…The bands observed at 3440 and 3159 cm -1 in the FT-IR and at 3475, 3445 and 3076 cm -1 in the FT Raman spectra with 100, 100, 100, 100 and 97% of PED contribution are attributed to the N-H groups of the pyrimidine ring. The theoretically-calculated values of the N-H vibrations by the B3LYP/6-311++G(d,P) in high frequency region are reliable with the experimental results and these assignments are in good agreement with the literature data [35].…”

Section: N-h Vibrationssupporting

confidence: 86%

“…1-[(2-Hydroxyethoxy)methyl]-6-(phenylthio)thymine (HEPT) and its related analogues [26][27][28][29] were discovered as potent and selectively active agents against HIV-1 infections. In continuation of our ongoing interest in the pharmacological and structural properties of pyrimidine and uracil derivatives [3,4,17,18,[30][31][32][33][34][35], we synthesized the title compound as the more lipophilic 5-propyl HEPT analog for evaluation as a potential chemotherapeutic agent [36].…”

Section: Introductionmentioning

confidence: 99%

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Molecular structure, vibrational spectra, NBO, Fukui function, HOMO-LUMO analysis and molecular docking study of 6-[(2-methylphenyl)sulfanyl]-5-propylpyrimidine-2,4(1H,3H)-dione

AlRabiah

Muthu²,

Al-Omary

et al. 2017

Maced. J. Chem. Chem. Eng.

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Theoretical and experimental FT-IR and FT-Raman vibrational spectral analysis of 6-[(2-methylphenyl)sulfanyl]-5-propylpyrimidine-2,4(1H,3H)-dione have been recorded in the region 4000-400 cm-1 and 4000-100 cm-1 insolid phase. The molecular geometrical parameters, bond length, bond angle and vibrational wave numbers, harmonic vibrational frequency were investigated using the density functional theory B3LYP method with the 6-311++G(d,p) basis set. The stability of the molecule has been investigated using the natural bond orbital (NBO) analysis. The electronic properties such as HOMO-LUMO energies were determined by the time-dependent DFT approach. The thermodynamical properties and the first order hyperpolarizability and molecular electrostatic potential (MEP) of the title compound were also studied. The electron density-based local reactivity descriptors such as the Fukui functions were calculated to explain the chemical selectivity or reactivity site in the molecule. The molecule orbital contributions were investigated using the total density of states (TDOS), the sum of 𝛼 and 𝛽 electron density of states (𝛼𝛽DOS). The molecular docking (ligand-protein) simulations have been performed using the SWISSDOCK server. The full fitness (FF) score and hydrogen bonding interaction and binding affinity values revealed that title compound can act as potential inhibitor against HIV-1 protease.

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Section: N-h Vibrationssupporting

confidence: 86%