Shekharagouda Pampapathi, Mamatha G P, Nagaraju G, Krishnamurthy Chethan, Gouthaman Siddan, Al-Asbahi Bandar Ali, Al-Hada Naif Mohammed, Naik Lohit
Department of Studies in Chemistry, Davangere University, Shivagangothri, 577 007, Davanagere, Karnataka, India.
Energy Material Research Laboratory, Department of Chemistry, Siddaganga Institute of Technology, Tumakuru, Karnataka, 572 103, India.
J Fluoresc. 2025 Feb;35(2):819-833. doi: 10.1007/s10895-023-03542-3. Epub 2024 Jan 6.
A series of unique four mono-azo substituted anthraquinone analogue were synthesized by using the anthraquinone components in the diazo-coupling technique. The FT-IR, H NMR, and HRMS, data were used to confirm the structure of the molecules, and spectroscopic techniques like UV-Vis, and photoluminescence spectroscopy were employed to estimate the photophysical properties of the molecules. The molecular optimized geometry and frontier molecular orbitals were estimated using density functional theory. Further, global chemical reactivity descriptors parameter was theoretically estimated using the value of the highest occupied molecular orbit and lowest unoccupied molecular orbits. The anti-tubercular action of the synthesised dyes were also examined. The results of this biological activity showed that N-isopropyl aniline combined with anthraquinone N-isopropyl aniline had superior anti-tubercular activity when compared to Rifampicin as the standard. As per molecular docking studies, the synthesized compound Q1 showed excellent binding energy (-10.0 kcal/mol) among all compounds against the 3ZXR Protein. These results agreed with our in-vitro anti-TB activity results.
通过在重氮偶合技术中使用蒽醌成分，合成了一系列独特的四种单偶氮取代蒽醌类似物。利用傅里叶变换红外光谱（FT-IR）、氢核磁共振（H NMR）和高分辨质谱（HRMS）数据确认分子结构，并采用紫外可见光谱（UV-Vis）和光致发光光谱等光谱技术评估分子的光物理性质。使用密度泛函理论估算分子的优化几何结构和前沿分子轨道。此外，利用最高占据分子轨道和最低未占据分子轨道的值从理论上估算全局化学反应性描述符参数。还考察了合成染料的抗结核作用。该生物活性结果表明，与作为标准的利福平相比，N-异丙基苯胺与蒽醌结合的N-异丙基苯胺具有优异的抗结核活性。根据分子对接研究，合成化合物Q1在所有化合物中对3ZXR蛋白显示出优异的结合能（-10.0千卡/摩尔）。这些结果与我们的体外抗结核活性结果一致。
