Synthesis And Bioactivities Of 4-O-β-D-glucopyranosyl-benzoxazolin-2(3H)-one And 4-Substituted Benzoxazolone Derivatives

The compounds of benzoxazolone were a special materiae which were occurring in the Gramineae,Acanthaceae,Ranunculaceae and Scrophulariaceae families.They were not only the defense compounds towards fungi,bacteria,pests,but also an important chemical mediate widely used in medicine.Chlorzoxazone(chemical name 5-chlorine benoxazolone),as center muscle relaxant,was antipyretic analgetic and non-steroid antiinflammatory which was widely use in clinic for its little adverse effect.Considerable structure modify and activity evaluation have been done because of difference activities,N-,5 or 6-phen for instance.We found that the reports of 4-substituted benzoxazolone were seldom.The compound 4-O-β-D-glucopyranosyl-benzoxazolin-2(3H)-one was a new compound separated from the plant Acanthus ilicifolius L.(Acanthaceae).The bioactivity showed that it had the activities of anti-bacterium,antiinflammatory and anti-hepatitis.Because of the new structure and the activity,we choosen 4-phen as a new deuterogenic position.We synthesised a series of 4-substituted benzoxazolone and estimated their activities in this article.2-aminoresorcinol as starting material was reacted with bis(trichloromethyl) carbonate to provide 4-hydroxy-benzoxazolone,followed by reaction with glycosyl bromide,acyl chloride,or Boc-amino acids to produce eighteen 4-substituted benzoxazolone derivatives.Structures of target compounds were confirmed by 1~H-NMR,(13)~C-NMR,ESI-MS and HR-MS spectra.The activities of antiinflammatory and analgetic were evaluated by the model of xylene-induced ear edema in mice and acetic acid-induced mice's writhing.The results showed that the compounds 3a,3b,4d,5a,5e,5g,5h,5j showed strong antiinflammatory effect and the compound 3a showed better analgetic effect.We provided a route for the further designing and synthesizing the benzoxazolone derivatives.