Microwave assisted palladium catalyzed carbon-carbon bond formation to synthesise novel benzimidazole derivatives and their Photophysical properties, molecular docking, and DFT study

微波辅助钯催化碳-碳键形成反应合成新型苯并咪唑衍生物及其光物理性质、分子对接和DFT研究

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Abstract

In the present study, novel benzimidazole compounds are synthesized, utilizing Suzuki coupling and acid-amine coupling reaction. The formation of all synthesized derivatives was confirmed through various spectroscopic techniques, including (1)H, (13)C, Carbon DEPT-135, H-H COSY, HSQC, and HRMS. The UV-Vis and fluorescence spectra of all synthesized compounds were recorded. Particularly, among all synthesized compounds, compound 9o (304.06 nm) exhibited the higher λ(max) in UV-Vis spectroscopy, while compound 9j (396.16 nm) exhibited the highest emmision intensity in fluorescence spectroscopy. Furthermore, density functional theory (DFT) calculations were performed at the B3LYP/6-31G'(d,p) foundational level set. These calculations aimed to predict the chemical reactivity of the newly synthesized benzimidazole derivatives by assessing parameters such as the HOMO-LUMO energy gap value, ionization potential, electrostaic potential, electron affinity, electronegativity, global hardness, and softness energy values. Subsequently, a molecular docking analysis was performed on all synthesized derivatives on a protein associated with Bcl-2 in conjunction with venetoclax, with compound 9g (-10.77 kcal/mol) indicating the most significant binding affinity among the compounds investigated.

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