Synthesis of phenyl-3- and phenyl-5-acetamidosalicylates as potential analgesics.
Phenylsalicylate was nitrated to obtain two nitro isomers, which were separated and reduced to the corresponding amines followed by acetylation to give phenyl-5- or phenyl-3-acetamidosalicylate. Phenyl-5-acetamidosalicylate displayed analgesic activity comparable to that of aspirin and phenacetin at doses of 25-50 mg/kg sc and was much less toxic than the latter compounds. Phenyl-3-acetamidosalicylate, however, was ineffective at a similar dose range and caused restlessness at larger doses.
D000107:Acetylation; D000588:Amines; D000700:Analgesics / Q000138:chemical synthesis*; D000818:Animals; D055598:Chemical Phenomena; D002621:Chemistry; D005260:Female; D008297:Male; D051379:Mice; D009574:Nitro Compounds; D010084:Oxidation-Reduction; D012459:Salicylates / Q000138:chemical synthesis* / Q000494:pharmacology / Q000633:toxicity
D000588:Amines; D000700:Analgesics; D009574:Nitro Compounds; D012459:Salicylates