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

Ambreen Zia; Syed Nawazish Ali; Erum Hasan; Mehreen Lateef; Syeda Rehana Zia; Sana Gul; Syeda Farah Bukhari; Nazish Dildar

doi:10.2174/1570179420666230724102756

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

Curr Org Synth. 2023 Sep 4. doi: 10.2174/1570179420666230724102756. Online ahead of print.

Authors

Ambreen Zia¹, Syed Nawazish Ali¹, Erum Hasan¹, Mehreen Lateef², Syeda Rehana Zia³, Sana Gul⁴, Syeda Farah Bukhari¹, Nazish Dildar¹

Affiliations

¹ Department of Chemistry, University of Karachi, Karachi-75270, Pakistan.
² Department of Biochemistry, Multi-Disciplinary Research Laboratory, Bahria University Medical and Dental College, Karachi- 75640, Pakistan.
³ Department of Pediatrics and Child Health, Medical College, The Aga Khan University, Karachi-74800, Pakistan.
⁴ Department of Chemistry, Faculty of Science, Federal Urdu University of Arts, Science and Technology, Gulshan-e-Iqbal Campus, University Road, Karachi-75300, Pakistan.

PMID: 37723957
DOI: 10.2174/1570179420666230724102756

Abstract

This study aimed to prepare three imine derivatives (1, 2, and 3) via a condensation reaction 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.

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