A Novel Method for the Syntheses of Imidazo-Thiadiazoles as Potential Antioxidants and Anti-Inflammatory Agents

Recent Adv Inflamm Allergy Drug Discov. 2022;16(1):19-25. doi: 10.2174/2772270816666220410130059.

Abstract

Background: A literature survey revealed that many imidazo-thiadiazole molecules were used as key intermediates for the development of novel drugs. The synthesized imidazo-thiadiazole derivatives were tested for their in vitro antioxidant and anti-inflammatory properties. The purpose of this research paper is to provide readers with information regarding diseases caused by free radicals.

Objective: The objective of this study is to develop novel antioxidant and anti-inflammatory drugs.

Methods: Imidazo-thiadiazole derivatives 5a-f were synthesized through cyclo-condensation reactions in two steps. First, the synthesis of 2-amino-thiadiazole derivatives from substituted aromatic carboxylic acids and thiosemicarbazide by using POCl3 as a solvent as well as a catalyst was performed. In the next step, imidazo-thiadiazoles were prepared from 2-amino-thiadiazole derivatives with appropriate α-haloketones in the presence of polyethylene glycol-300 (PEG-300) as a green solvent. These imidazo- thiadiazole derivatives were prepared by using a novel method. The synthesized compounds were in vitro tested for their antioxidant and anti-inflammatory activities.

Results: In vitro evaluation report showed that nearly all molecules possess potential antioxidant activity against 2,2-diphenyl-1-picrylhydrazyl (DPPH), nitric oxide (NO), superoxide radical (SOR), and hydrogen peroxide (H2O2) radical scavenging activity. Most of the imidazo-thiadiazole derivatives have shown significant anti-inflammatory activity as compared to diclofenac sodium as a reference standard.

Conclusion: In the search for novel therapies to treat inflammation and oxidation, we have made efforts to develop anti-inflammatory and antioxidant agents with a preeminent activity. Imidazo-thiadiazoles 5a, 5e as well as 5f showed potential anti-inflammatory activity. All tested imidazo-thiadiazole deriv-atives (5a-f) showed potential antioxidant activity against one more radical scavenging species as com-pared to ascorbic acid as the reference standard. Thus, imidazo-thiadiazole derivatives constitute an interesting template for the design and development of new antioxidant as well as anti-inflammatory agents.

Keywords: Biological evaluations; anti-inflammatory activity; antioxidant activity; bis-imidazo thiadiazoles derivatives; imidazo thiadiazoles derivatives; polycyclic aromatic compounds.

MeSH terms

  • Anti-Inflammatory Agents / pharmacology
  • Antioxidants / pharmacology
  • Ascorbic Acid
  • Hydrogen Peroxide
  • Thiadiazoles* / pharmacology

Substances

  • Thiadiazoles
  • Antioxidants
  • Hydrogen Peroxide
  • Anti-Inflammatory Agents
  • Ascorbic Acid