Syntheses and antibacterial activities of tizoxanide, an N-(nitrothiazolyl)salicylamide, and its O-aryl glucuronide

Mild hydrolysis of the broad-spectrum anaerobic antibacterial and antiparas itic agent nitazoxanide 1 affords tizoxanide 2, which is a major metabolite of 1 retaining most of its activity; further metabolism of 2 leads to the O-aryl glucuronide 3, efficiently synthesised in four steps from benzyl sal icylate and showing slight antibacterial activity.