Chavan Nagesh Dhanaji, Sarveswari S, Vijayakumar V
Department of Chemistry, School of Advanced Sciences, Vellore Institute of Technology, Vellore, 632014, India.
Sci Rep. 2025 Mar 31;15(1):10972. doi: 10.1038/s41598-025-94817-1.
The synthesis of new quinoline-sulphonamide derivatives was accomplished through a meticulous five-step molecular assembly utilizing Suzuki, acid-amine cross-coupling reactions and N-alkylation. The integrity of each derivative was thoroughly confirmed via comprehensive spectroscopic analyses, including H and C NMR, DEPT-135, H-H COSY, HSQC NMR and HRMS techniques. Subsequently, the absorbance and emission spectra of the newly synthesized derivatives were thoroughly investigated. Absorbance spectra were determined to be restricted within the range of 337 nm to 341.73 nm, with compound 10j exhibiting the maximum wavelength of 341.73 nm; conversely, emission spectra were uniformly detected within the range of 411.70 nm to 429.90 nm upon excitation at 340 nm, with compound 10f demonstrating the highest wavelength of 429.90 nm. Notably, these fluorophores displayed impressive characteristics, with high intensity and significant molar extinction coefficients; quantum yield ranging from 0.015 to 0.558 along with the highest stokes shifts in 10h compound (0.6237 × 10) in acetonitrile solvent. Additionally, compound 10p showed strong binding affinity and favorable pharmacokinetic properties through molecular docking studies and ADMET calculations. The electronic structure of the molecules was elucidated using techniques such as density functional theory (DFT) and molecular electrostatic potential (MEP) mapping. Additionally, the calculated global reactivity parameters provided valuable insights. Compound 10p exhibited a distinctly low energy gap compared to other compounds, demonstrating its exceptional properties. The comparison between experimental and theoretical UV-vis spectra with major contribution transition in percentage also showcased the remarkable consistency and quality of the synthesized derivatives, highlighting the significant potential of this work in the field of fluorophore and biological application.
通过使用铃木反应、酸 - 胺交叉偶联反应和N - 烷基化进行细致的五步分子组装，完成了新型喹啉 - 磺酰胺衍生物的合成。通过全面的光谱分析，包括H和C NMR、DEPT - 135、H - H COSY、HSQC NMR和HRMS技术，彻底确认了每种衍生物的完整性。随后，对新合成的衍生物的吸收光谱和发射光谱进行了深入研究。吸收光谱被确定限制在337 nm至341.73 nm范围内，化合物10j表现出最大波长341.73 nm；相反，在340 nm激发下，发射光谱在411.70 nm至429.90 nm范围内均匀检测到，化合物10f表现出最高波长429.90 nm。值得注意的是，这些荧光团显示出令人印象深刻的特性，具有高强度和显著的摩尔消光系数；量子产率范围为0.015至0.558，并且在乙腈溶剂中10h化合物具有最高的斯托克斯位移（0.6237×10）。此外，通过分子对接研究和ADMET计算，化合物10p显示出很强的结合亲和力和良好的药代动力学性质。使用密度泛函理论（DFT）和分子静电势（MEP）映射等技术阐明了分子的电子结构。此外，计算出的全局反应性参数提供了有价值的见解。与其他化合物相比，化合物10p表现出明显较低的能隙，证明了其优异的性能。实验和理论紫外 - 可见光谱之间的比较以及主要贡献跃迁的百分比也展示了合成衍生物的显著一致性和质量，突出了这项工作在荧光团和生物应用领域的巨大潜力。
