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Structural and spectral investigations of the recently synthesized chalcone (E)-3-mesityl-1-(naphthalen-2-yl) prop-2-en-1-one, a potential chemotherapeutic agent.

Barakat A, Al-Majid AM, Soliman SM, Mabkhot YN, Ali M, Ghabbour HA, Fun HK, Wadood A - Chem Cent J (2015)

Bottom Line: The calculated IR fundamental bands were assigned and compared with the experimental data.Molecular stability was successfully analyzed using NBO and electron delocalization is confirmed by MEP.Graphical Abstract(E)-3-Mesityl-1-(naphthalen-2-yl) prop-2-en-1-one: a crystal structure and computational studies.

View Article: PubMed Central - PubMed

Affiliation: Department of Chemistry, College of Science, King Saud University, P.O. Box 2455, 11451 Riyadh, Saudi Arabia ; Department of Chemistry, Faculty of Science, Alexandria University, P.O. Box 426, 21321 Alexandria, Ibrahimia Egypt.

ABSTRACT

Background: Chalcones (1,3-diaryl-2-propen-1-ones, represent an important subgroup of the polyphenolic family, which have shown a wide spectrum of medical and industrial application. Due to their redundancy in plants and ease of preparation, this category of molecules has inspired considerable attention for potential therapeutic uses. They are also effective in vivo as anti-tumor promoting, cell proliferating inhibitors and chemo preventing agents.

Results: Synthesis and molecular structure investigation of (E)-3-mesityl-1-(naphthalen-2-yl) prop-2-en-1-one (3) is reported. The structure of the title compound 3 is confirmed by X-ray crystallography. The optimized molecular structure of the studied compound is calculated using DFT B3LYP/6-311G (d,p) method. The calculated geometric parameters are in good agreement with the experimental data obtained from our reported X-ay structure. The calculated IR fundamental bands were assigned and compared with the experimental data. The electronic spectra of the studied compound have been calculated using the time dependant density functional theory (TD-DFT). The longest wavelength band is due to H → L (79 %) electronic transition which belongs to π-π* excitation. The (1)H- and (13)C-NMR chemical shifts were calculated using gauge independent atomic orbitals (GIAO) method, which showed good correlations with the experimental data (R(2) = 0.9911-0.9965). The natural bond orbital (NBO) calculations were performed to predict the natural atomic charges at different atomic sites. The molecular electrostatic potential (MEP) was used to visualize the charge distribution on the molecule. Molecular docking results suggest that the compound might exhibit inhibitory activity against GPb and may act as potential anti-diabetic compound.

Conclusions: (E)-3-Mesityl-1-(naphthalen-2-yl) prop-2-en-1-one single crystal is grown and characterized by single crystal X-ray diffraction, FT-IR, UV-vis, DFT and optimized geometrical parameters are close to the experimental bond lengths and angles. Molecular stability was successfully analyzed using NBO and electron delocalization is confirmed by MEP. Prediction of Activity Spectra Analysis of the title compound, predicts anti-diabetic activity with probability to have an active value of 0.348. Graphical Abstract(E)-3-Mesityl-1-(naphthalen-2-yl) prop-2-en-1-one: a crystal structure and computational studies.

No MeSH data available.


Related in: MedlinePlus

Comparison between the calculated and experimental geometric parameters (bond distances and bond angles) of 3
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Fig4: Comparison between the calculated and experimental geometric parameters (bond distances and bond angles) of 3

Mentions: The optimized bond lengths and bond angles obtained for the studied compound using the B3LYP method with 6–311G (d,p) basis set are given in Table 3; while the atom numbering of the optimized structure is given in Fig. 3. The studied compound possesses C1 point group. The optimized geometric parameters of the studied compound are compared with those obtained from the crystallographic information file (CIF) as shown in Fig. 4. Some of these geometric parameters are overestimated while the others are underestimated. The maximum deviations of the calculated bond length and bond angle values from the experimental data are 0.005–0.007 Å (O1–Cl9 and C19–C20) and 1.058° (O1–C19–C20) respectively. These little deviations are attributed to the phase difference between the calculated and the experimental data. The root mean square deviation (RMSD), the percentage relative error and the correlation coefficient (R2) values between the experimental and calculated bond distances are found to be 0.003 Å, 0.492 % and 0.9989, respectively. Generally, the bond lengths and bond angles are predicted very well.Table 3


Structural and spectral investigations of the recently synthesized chalcone (E)-3-mesityl-1-(naphthalen-2-yl) prop-2-en-1-one, a potential chemotherapeutic agent.

Barakat A, Al-Majid AM, Soliman SM, Mabkhot YN, Ali M, Ghabbour HA, Fun HK, Wadood A - Chem Cent J (2015)

Comparison between the calculated and experimental geometric parameters (bond distances and bond angles) of 3
© Copyright Policy - open-access
Related In: Results  -  Collection

License 1 - License 2
Show All Figures
getmorefigures.php?uid=PMC4477317&req=5

Fig4: Comparison between the calculated and experimental geometric parameters (bond distances and bond angles) of 3
Mentions: The optimized bond lengths and bond angles obtained for the studied compound using the B3LYP method with 6–311G (d,p) basis set are given in Table 3; while the atom numbering of the optimized structure is given in Fig. 3. The studied compound possesses C1 point group. The optimized geometric parameters of the studied compound are compared with those obtained from the crystallographic information file (CIF) as shown in Fig. 4. Some of these geometric parameters are overestimated while the others are underestimated. The maximum deviations of the calculated bond length and bond angle values from the experimental data are 0.005–0.007 Å (O1–Cl9 and C19–C20) and 1.058° (O1–C19–C20) respectively. These little deviations are attributed to the phase difference between the calculated and the experimental data. The root mean square deviation (RMSD), the percentage relative error and the correlation coefficient (R2) values between the experimental and calculated bond distances are found to be 0.003 Å, 0.492 % and 0.9989, respectively. Generally, the bond lengths and bond angles are predicted very well.Table 3

Bottom Line: The calculated IR fundamental bands were assigned and compared with the experimental data.Molecular stability was successfully analyzed using NBO and electron delocalization is confirmed by MEP.Graphical Abstract(E)-3-Mesityl-1-(naphthalen-2-yl) prop-2-en-1-one: a crystal structure and computational studies.

View Article: PubMed Central - PubMed

Affiliation: Department of Chemistry, College of Science, King Saud University, P.O. Box 2455, 11451 Riyadh, Saudi Arabia ; Department of Chemistry, Faculty of Science, Alexandria University, P.O. Box 426, 21321 Alexandria, Ibrahimia Egypt.

ABSTRACT

Background: Chalcones (1,3-diaryl-2-propen-1-ones, represent an important subgroup of the polyphenolic family, which have shown a wide spectrum of medical and industrial application. Due to their redundancy in plants and ease of preparation, this category of molecules has inspired considerable attention for potential therapeutic uses. They are also effective in vivo as anti-tumor promoting, cell proliferating inhibitors and chemo preventing agents.

Results: Synthesis and molecular structure investigation of (E)-3-mesityl-1-(naphthalen-2-yl) prop-2-en-1-one (3) is reported. The structure of the title compound 3 is confirmed by X-ray crystallography. The optimized molecular structure of the studied compound is calculated using DFT B3LYP/6-311G (d,p) method. The calculated geometric parameters are in good agreement with the experimental data obtained from our reported X-ay structure. The calculated IR fundamental bands were assigned and compared with the experimental data. The electronic spectra of the studied compound have been calculated using the time dependant density functional theory (TD-DFT). The longest wavelength band is due to H → L (79 %) electronic transition which belongs to π-π* excitation. The (1)H- and (13)C-NMR chemical shifts were calculated using gauge independent atomic orbitals (GIAO) method, which showed good correlations with the experimental data (R(2) = 0.9911-0.9965). The natural bond orbital (NBO) calculations were performed to predict the natural atomic charges at different atomic sites. The molecular electrostatic potential (MEP) was used to visualize the charge distribution on the molecule. Molecular docking results suggest that the compound might exhibit inhibitory activity against GPb and may act as potential anti-diabetic compound.

Conclusions: (E)-3-Mesityl-1-(naphthalen-2-yl) prop-2-en-1-one single crystal is grown and characterized by single crystal X-ray diffraction, FT-IR, UV-vis, DFT and optimized geometrical parameters are close to the experimental bond lengths and angles. Molecular stability was successfully analyzed using NBO and electron delocalization is confirmed by MEP. Prediction of Activity Spectra Analysis of the title compound, predicts anti-diabetic activity with probability to have an active value of 0.348. Graphical Abstract(E)-3-Mesityl-1-(naphthalen-2-yl) prop-2-en-1-one: a crystal structure and computational studies.

No MeSH data available.


Related in: MedlinePlus