Abedin Md Minhazul, Pal Tarun Kumar, Uddin Md Najem, Alim Mohammad Abdul, Sheikh Md Chanmiya, Paul Subrata
Department of Chemistry, Rajshahi University of Engineering & Technology, 6204, Bangladesh.
Pharmaceutical Sciences Research Division, BCSIR Laboratories (Dhaka), Bangladesh Council of Scientific and Industrial Research (BCSIR), Bangladesh.
Heliyon. 2024 Jul 14;10(14):e34556. doi: 10.1016/j.heliyon.2024.e34556. eCollection 2024 Jul 30.
The sulfonamide Schiff base compound (E)-4-((4-(dimethylamino)benzylidene)amino)-N-(5-methylisoxazol-3-yl)benzenesulfonamide was successfully prepared and fully characterized. The foremost objective of this study was to explore the molecular geometry of the aforementioned compound and determine its drug likeness characteristics, docking ability as an insulysin inhibitor, anticancer and antioxidant activities. The molecular structure of this compound was optimized using the B3LYP/6-311G+(d,p) level of theory. The compound was completely characterized utilizing both experimental and DFT approaches. Molecular electrostatic potential, frontier molecular orbitals, Fukui function, drug likeness, and in silico molecular docking analyses of this compound were performed. Wave functional properties such as localized orbital locator, electron localization function and non-covalent interactions were also simulated. The compound was screened for anticancer and antioxidant activities using in vitro technique. The observed FT-IR, UV-Vis, and H NMR results compared with simulated data and both results were fairly consistent. The experimental and computational spectral findings confirm the formation of the Schiff base compound. Both π-π* and n-π* transitions were observed in both experimental and computational UV-Vis spectra. The examined compound followed to Pfizer, Golden Triangle, GSK, and Lipinski's rules. Consequently, it possesses a more favorable absorption, distribution, metabolism, excretion, and toxicity (ADMET) profile, making it a suitable candidate for non-toxic oral drug use. Moreover, the compound exhibited promising insulysin inhibition activity in an in silico molecular docking. The compound showed in vitro anticancer activity against A549 cancer cells with an IC value of 40.89 μg/mL and moderate antioxidant activity.
成功制备了磺酰胺席夫碱化合物（E）-4-（（4-（二甲基氨基）亚苄基）氨基）-N-（5-甲基异恶唑-3-基）苯磺酰胺并对其进行了全面表征。本研究的首要目标是探索上述化合物的分子几何结构，确定其类药特性、作为胰岛素溶酶抑制剂的对接能力、抗癌和抗氧化活性。使用B3LYP/6-311G+（d，p）理论水平对该化合物的分子结构进行了优化。利用实验和密度泛函理论（DFT）方法对该化合物进行了全面表征。对该化合物进行了分子静电势、前沿分子轨道、福井函数、类药性质和计算机辅助分子对接分析。还模拟了诸如定域轨道定位器、电子定域函数和非共价相互作用等波函数性质。采用体外技术对该化合物进行了抗癌和抗氧化活性筛选。将观察到的傅里叶变换红外光谱（FT-IR）、紫外可见光谱（UV-Vis）和氢核磁共振（H NMR）结果与模拟数据进行了比较，两者结果相当一致。实验和计算光谱结果证实了席夫碱化合物的形成。在实验和计算的紫外可见光谱中均观察到了π-π和n-π跃迁。所研究的化合物符合辉瑞、金三角、葛兰素史克和Lipinski规则。因此，它具有更有利的吸收、分布、代谢、排泄和毒性（ADMET）特征，使其成为无毒口服药物的合适候选物。此外，该化合物在计算机辅助分子对接中表现出有前景的胰岛素溶酶抑制活性。该化合物对A549癌细胞表现出体外抗癌活性，IC值为40.89μg/mL，并且具有中等抗氧化活性。
