Barakat Assem, Al-Majid Abdullah Mohammed, Soliman Saied M, Mabkhot Yahia Nasser, Ali M, Ghabbour Hazem A, Fun Hoong-Kun, Wadood Abdul
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.
Department of Chemistry, College of Science, King Saud University, P.O. Box 2455, 11451 Riyadh, Saudi Arabia.
Chem Cent J. 2015 Jun 13;9:35. doi: 10.1186/s13065-015-0112-5. eCollection 2015.
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.
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.
(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.
查耳酮（1,3 - 二芳基 - 2 - 丙烯 - 1 - 酮）是多酚家族的一个重要亚组，已显示出广泛的医学和工业应用。由于它们在植物中的冗余性和易于制备，这类分子引发了对其潜在治疗用途的相当大关注。它们在体内作为抗肿瘤促进剂、细胞增殖抑制剂和化学预防剂也很有效。
报道了（E）-3 - 均三甲苯基 - 1 -（萘 - 2 - 基）丙 - 2 - 烯 - 1 - 酮（3）的合成及分子结构研究。通过X射线晶体学确定了标题化合物3的结构。使用DFT B3LYP/6 - 311G（d,p）方法计算了所研究化合物的优化分子结构。计算得到的几何参数与从我们报道的X射线结构获得的实验数据吻合良好。对计算得到的红外基本谱带进行了归属并与实验数据进行了比较。使用含时密度泛函理论（TD - DFT）计算了所研究化合物的电子光谱。最长波长带归因于H→L（79%）电子跃迁，属于π - π*激发。使用规范无关原子轨道（GIAO）方法计算了（1）H - 和（13）C - NMR化学位移，其与实验数据显示出良好的相关性（R² = 0.9911 - 0.9965）。进行了自然键轨道（NBO）计算以预测不同原子位点的自然原子电荷。使用分子静电势（MEP）来可视化分子上的电荷分布。分子对接结果表明该化合物可能对GPb表现出抑制活性，并可能作为潜在的抗糖尿病化合物。
生长了（E）-3 - 均三甲苯基 - 1 -（萘 - 2 - 基）丙 - 2 - 烯 - 1 - 酮单晶，并通过单晶X射线衍射、傅里叶变换红外光谱（FT - IR）、紫外 - 可见光谱（UV - vis）、密度泛函理论（DFT）进行了表征，优化的几何参数接近实验键长和键角。使用NBO成功分析了分子稳定性，通过MEP证实了电子离域。对标题化合物的活性谱分析预测，其具有抗糖尿病活性，活性值为0.348的概率。图形摘要（E）-3 - 均三甲苯基 - 1 -（萘 - 2 - 基）丙 - 2 - 烯 - 1 - 酮：晶体结构与计算研究。
