5-(Alkylsulfonyl)salicylanilides as potential dental antiplaque agents.
A series of 22 5-(alkylsulfonyl)salicylanilides was synthesized and evaluated for in vitro antibacterial and antiplaque activity against Actinomyces viscosus and Streptococcus mutans, adherent microorganisms implicated in periodontal disease and dental caries. The minimum inhibitory concentrations of 25 salicylanilides (including 5-acyl-, 5-alkyl-, and 5-(alkylsulfonyl)-4'-bromo- and -4'-(trifluoromethyl)salicylanilides) were found to correlate (r = 0.94) with estimated log D values. Several salicylanilides, such as 5-(decylsulfonyl)- and 5-(dodecylsulfonyl)-4'-(trifluoromethyl)salicylanilides (15 and 19) were found to exhibit high levels of in vitro antibacterial and antiplaque activity against A. viscosus and S. mutans.
D000190:Actinomyces / Q000187:drug effects; D000818:Animals; D002417:Cattle; D003773:Dental Plaque / Q000517:prevention & control*; D008826:Microbial Sensitivity Tests; D012457:Salicylamides / Q000627:therapeutic use*; D012458:Salicylanilides / Q000138:chemical synthesis / Q000494:pharmacology / Q000627:therapeutic use*; D013295:Streptococcus mutans / Q000187:drug effects; D013329:Structure-Activity Relationship
D012457:Salicylamides; D012458:Salicylanilides