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. 2024 May 21;10(10):e31563.
doi: 10.1016/j.heliyon.2024.e31563. eCollection 2024 May 30.

Antioxidant, antibacterial, enzyme inhibition and fluorescence characteristics of unsymmetrical thiourea derivatives

Faizan Ur Rahman  1 , Abdul Bari Shah  2 , Mian Muhammad  1 , Ezzat Khan  1 , Farid S Ataya  3 , Gaber El-Saber Batiha  4
Affiliations

Antioxidant, antibacterial, enzyme inhibition and fluorescence characteristics of unsymmetrical thiourea derivatives

Faizan Ur Rahman et al. Heliyon. .

Abstract

A series of six unsymmetrical thiourea derivatives, namely 1-cyclohexyl-3-(pyridin-2-yl) thiourea (1), 1-cyclohexyl-3-(3-methylpyridin-2-yl)thiourea (2), 1-cyclohexyl-3-(2,4-dimethylphenyl) thiourea (3), 1-(4-chlorophenyl)-3-cyclohexylthiourea (4), 1-(3-methylpyridin-2-yl)-3-phenylthiourea (5), and 1-(3-chlorophenyl)-3-phenylthiourea (6), were successfully synthesized via reaction between different amines with isothiocyanates under a non-catalytic environment. Structural elucidation of compounds (1-6) was performed using FT-IR and NMR (1H and 13C) spectroscopy. The infrared spectra displayed characteristic stretching vibrations, while the 13C NMR chemical shifts of the thiourea moiety (C[bond, double bond]S) were observed in the range of 179.1-181.4 ppm. The antioxidative and antimicrobial properties of the compounds were assessed, as well as their inhibitory effects on acetylcholinesterase and butyrylcholinesterase were evaluated. In order to analyze the fluorescence characteristics of each compound (1-6), the excitation (λex) and emission (λem) wavelengths were scanned within the range of 250-750 nm, with the solvent blank serving as a standard. It was observed that when dissolved in acetone, toluene, tetrahydrofuran, and ethyl acetate, these compounds exhibited emission peaks ranging from 367 to 581 nm and absorption peaks ranging from 275 to 432 nm.

Keywords: Antimicrobial; Enzyme inhibition; Fluorescence characteristics; Free radical scavenging; Structural characterization; Thiourea derivatives; Unsymmetrical thioureas.

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Conflict of interest statement

The authors declare that they have no known competing financial interests or personal relationships that could have appeared to influence the work reported in this paper.

Figures

Fig. 1
Fig. 1
Structure of synthesized compounds (1–6) used in this study.
Fig. 2
Fig. 2
Fluorescence spectra of compounds. Each compound is represented by their number from 1–6.
Fig. 3
Fig. 3
Fluorescence intensity of F16 as a function of the concentration of Hg(II); Curves e:no Hg(II) added, Curve d, c, b, a:0.01, 0.02, 0.03, 0.04 (μg mL−1) Hg(II) added.
Fig. 4
Fig. 4
Investigation of the interaction of Compounds (1–6) with Hg(II).
Fig. 5
Fig. 5
Investigation of the interaction of metal ions with compound 3.
See this image and copyright information in PMC

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