Unsymmetrical Thiourea Derivatives: Synthesis and Evaluation as Promising Antioxidant and Enzyme Inhibitors

Abstract

Background:

Unsymmetrical thioureas 1–20 were synthesized and then characterized by various spectroscopy techniques such as UV, IR, fast atom bombardment (FAB)-MS, high-resolution FAB-MS, ¹H-NMR and ¹³C-NMR.

Methods:

Synthetic compounds 1–20 were tested for their ability for antioxidant, lipoxygenase and xanthine oxidase activities.

Results:

Compounds 1, 2, 9, 12 and 15 exhibited strong antioxidant potential, whereas compounds 1–3, 9, 12, 15 and 19 showed good to moderate lipoxygenase activity. Ten compounds demonstrated moderate xanthine oxidase inhibition.

Conclusion:

Compound 15 displayed the highest potency among the series, exhibiting good antioxidant, lipoxygenase and xanthine oxidase activities. Theoretical calculations using density functional theory and molecular docking studies supported the experimental findings, indicating the potential of the synthesized compounds as potent antioxidants, lipoxygenases and xanthine oxidase agents.

Keywords::

• antioxidant
• lipoxygenase
• unsymmetrical thiourea
• xanthine oxidase

Supplementary data

To view the supplementary data that accompany this paper please visit the journal website at: www.tandfonline.com/doi/suppl/10.4155/fmc-2023-0213

Author contributions

B Bano and Kanwal: conceptualization, methodology, biological experiments, project administration and writing of the original draft. KM Khan: supervision, conceptualization, visualization, resources, project administration, methodology, investigation, funding acquisition, formal analysis, review, editing and validation of the final draft of the manuscript. A Wadood and M Lateef: investigation of biological experiments, methodology and writing of the original draft. S Hussain and S Shams: investigation on bioassays and methodology. S Hameed: writing review and editing of the draft, spectroscopic data analysis, quality control and validation of manuscript. NUI Ain, S Perveen and M Taha: supervised all the synthetic work, quality control, characterization of spectra and initial draft of the synthetic part of the manuscript. All authors revised and approved the final draft and data analysis. All authors have read and agreed to the published version of the manuscript.

Financial disclosure

The authors acknowledge the financial support of the Sindh Higher Education Commission (SHEC), Pakistan, vide letter No. NO.DD/SHEC/1-14/2014, Project code SHEC/SRSP/Med-3/15/2021-21. The authors have no other relevant affiliations or financial involvement with any organization or entity with a financial interest in or financial conflict with the subject matter or materials discussed in the manuscript apart from those disclosed.

Competing interests disclosure

The authors have no competing interests or relevant affiliations with any organization or entity with the subject matter or materials discussed in the manuscript. This includes employment, consultancies, honoraria, stock ownership or options, expert testimony, grants or patents received or pending, or royalties.

Writing disclosure

No writing assistance was utilized in the production of this manuscript.

Data availability statement

The data supporting this study’s findings are available from the corresponding author upon reasonable request.