Synthesis, Characterization, DPPH Radical Scavenging, Urease Enzyme Inhibition, Molecular Docking Simulation, and DFT Analysis of Imine Derivatives of 4-formylpyridine with Selective Detection of Cu⁺² Ions

Title:Synthesis, Characterization, DPPH Radical Scavenging, Urease Enzyme Inhibition, Molecular Docking Simulation, and DFT Analysis of Imine Derivatives of 4-formylpyridine with Selective Detection of Cu⁺² Ions

Volume: 21 Issue: 6

Author(s): Ambreen Zia, Syed Nawazish Ali*, Erum Hasan, Mehreen Lateef, Syeda Rehana Zia, Sana Gul, Syeda Farah Bukhari and Nazish Dildar

Affiliation:

• Department of Chemistry, University of Karachi, Karachi, 75270, Pakistan

Keywords: 4-formylpyridine, imines, copper ion detection, DPPH, urease inhibition, molecular docking simulation, DFT.

Abstract: This study aimed to prepare three imine derivatives (1, 2, and 3) via a condensation reac-tion of phenyl hydrazine, 2-hydrazino pyridine, and 4-methoxy aniline with 4-formyl pyridine. Electron impact mass spectrometry (EIMS), proton nuclear magnetic resonance (¹H-NMR), ultraviolet-visible (UV-Vis) and Fourier transform infrared (FTIR) spectroscopy were utilized for the characterization. The chemosensing properties of [4((2-phenyl hydrazono)methyl) pyridine] (1), [2-(2-(pyridin-4-ylmethylene)hydrazinyl) pyridine] (2), and [4-methoxy-N-yl methylene) aniline] (3) imino bases have been explored for the first time in aqueous media. The photophysical properties of chemosensors (1, 2, and 3) were examined by various cations (Na⁺, NH4⁺, Ba⁺2, Ni⁺2, Ca⁺2, Hg⁺2, Cu⁺2, Mg⁺2, Mn⁺2, and Pd⁺2). The chemosensor (1) showed very selective binding capability with copper ions at low concentrations (20 μM) without the influence of any other mentioned ions. The maximum complexation was noted with Cu⁺2 and 1 at pH between 7 to 7.5. The stoichiometry binding ratio between chemosensor (1) and Cu⁺2 was determined by Job’s plot and it was found to be 1:2. The current study explored the use of these Schiff bases for the first time as heterocyclic chemosensors. DPPH radical scavenging, urease enzyme inhibition activities, molecular docking simulation, and density functional theory (DFT) analysis of compounds 1, 2, and 3 were also conducted.

Cite this article as:

Zia Ambreen, Ali Nawazish Syed*, Hasan Erum, Lateef Mehreen, Zia Rehana Syeda, Gul Sana, Bukhari Farah Syeda and Dildar Nazish, Synthesis, Characterization, DPPH Radical Scavenging, Urease Enzyme Inhibition, Molecular Docking Simulation, and DFT Analysis of Imine Derivatives of 4-formylpyridine with Selective Detection of Cu⁺² Ions, Current Organic Synthesis 2024; 21 (6) . https://dx.doi.org/10.2174/1570179420666230724102756