Synthesis and evaluation of ursolic acid-based 1,2,4-triazolo[1,5-a]pyrimidines derivatives as anti-inflammatory agents

Mol Divers. 2022 Feb;26(1):27-38. doi: 10.1007/s11030-020-10154-7. Epub 2020 Nov 17.

Abstract

Here, two series of novel ursolic acid-based 1,2,4-triazolo[1,5-a]pyrimidines derivatives were synthesized and screened for their anti-inflammatory activity by evaluating their inhibition effect of using LPS-induced inflammatory response in RAW 264.7 macrophages in vitro; the effects of different concentrations of the compounds on the secretion of nitric oxide (NO) and inflammatory cytokines including TNF-α and IL-6 were evaluated. Their toxicity was also assessed in vitro. Results showed that the most prominent compound 3 could significantly decrease production of the above inflammatory factors. Docking study was performed for the representative compounds 3, UA, and Celecoxib to explain their interaction with cyclooxygenase-2 (COX-2) receptor active site. In vitro enzyme study implied that compound 3 exerted its anti-inflammatory activity through COX-2 inhibition.

Keywords: Anti-inflammatory activity; COX-2 inhibition; Molecular modeling; Ursolic acid.

MeSH terms

  • Anti-Inflammatory Agents* / chemistry
  • Cyclooxygenase 2 / metabolism
  • Lipopolysaccharides / toxicity
  • Molecular Docking Simulation
  • Pyrimidines* / pharmacology
  • Structure-Activity Relationship
  • Triterpenes
  • Ursolic Acid

Substances

  • Anti-Inflammatory Agents
  • Lipopolysaccharides
  • Pyrimidines
  • Triterpenes
  • Cyclooxygenase 2