Synthesis and studies molecular docking of some new thioxobenzo[g]pteridine derivatives and 1,4-dihydroquinoxaline derivatives with glycosidic moiety

Abstract

The present work is mainly dedicated to heterocyclic compounds as well as S-glycoside. 1,4-dihydroquinoxaline derivatives 3 were obtained from the reaction 2 with carbon disulfide in presence of potassium hydroxide. S-glycoside 4 was prepared from the reaction of compound 3 with 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide. Several heterocyclic derivatives containing thioxobenzo[g]pteridine ring systems were obtained starting from ethyl 3-amino-1,4-dihydroquinoxaline-2-carboxylate 1. These newly synthesized compounds were docked within the active site of cyclooxygenase-2 (COX-2). The results of this docking study revealed that the new compounds might exhibit good anti-inflammatory activity. The structure of new compounds was demonstrated by elemental analysis, IR, 1H NMR spectra and mass spectra.

Keywords

• Thioxobenzo[g]pteridine
• 1,4-dihydroquinoxalin
• Synthesis
• Glycosylation
• S-glycosides and molecular docking