Molecular modeling, enzyme activity, anti-inflammatory and antiarthritic activities of newly synthesized quinazoline derivatives

Future Med Chem. 2017 Nov;9(17):1995-2009. doi: 10.4155/fmc-2017-0157. Epub 2017 Aug 9.

Abstract

Aim: 16 thioxoquinazolines were evaluated in vivo for anti-inflammatory activity using carrageenan-induced paw edema assay.

Results: In particular, out of the targets (1-16), compounds 4 and 6 displayed the highest anti-inflammatory activity (≥80%) and furtherly tested against complete Freund's adjuvant-induced arthritic rats. Significant reduction in the serum level of IL-1β, COX-2 and prostaglandin E2 in the complete Freund's adjuvant rats is demonstrated by compounds 4 and 6. Furthermore, compound 4 showed non-selective activity against COX-1 and COX 2, however, compound 6 was specific toward COX-2. Molecular docking study has demonstrated the possible binding modes of the active quinazolines 4 and 6 in the COX-2 active site.

Conclusion: These targets could be used as templates for further development of new derivatives with potent anti-inflammatory activity.

Keywords: 2-thioxoquinazolin-4-(3H)-one; anti-inflammatory; antiarthritic; molecular modeling.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Antirheumatic Agents / chemical synthesis
  • Antirheumatic Agents / chemistry
  • Antirheumatic Agents / pharmacology*
  • Arthritis, Experimental / drug therapy*
  • Carrageenan
  • Cyclooxygenase 1 / metabolism
  • Cyclooxygenase 2 / metabolism
  • Cyclooxygenase Inhibitors / chemical synthesis
  • Cyclooxygenase Inhibitors / chemistry
  • Cyclooxygenase Inhibitors / pharmacology*
  • Dose-Response Relationship, Drug
  • Edema / chemically induced
  • Edema / drug therapy*
  • Membrane Proteins / antagonists & inhibitors
  • Membrane Proteins / metabolism
  • Molecular Docking Simulation
  • Molecular Structure
  • Quinazolines / chemical synthesis
  • Quinazolines / chemistry
  • Quinazolines / pharmacology*
  • Rats
  • Structure-Activity Relationship

Substances

  • Antirheumatic Agents
  • Cyclooxygenase Inhibitors
  • Membrane Proteins
  • Quinazolines
  • Carrageenan
  • Cyclooxygenase 1
  • Cyclooxygenase 2
  • Ptgs1 protein, rat
  • Ptgs2 protein, rat