Studies on the Syntheses and Antibacterial Activity of Thiohydantoin Related Compounds. XI. : Syntheses of 3-Amino-4-thiohydantoic Acid Hydrazide Derivatives.

Abstract

3-Amino-4-thiohydantoic acid hydrazide (VI) was obtained by the reaction of ethyl 3-amino-4-thiohydantoate (IV) or 1-amino-2-thiohydantoin (V) with hydrazine hydrate. Reaction of IV or V with aromatic aldehydes gave various kinds of benzylidene compounds (VII to XII or XIII to XVIII) which were reacted with hydrazine hydrate to give 3-benzylideneamino-4-thiohydantoic acid hydrazides (XIX to XXIV). Treatment of the compounds VII to XII, and XIX to XXIV with hydrochloric acid resulted in their cyclization to 1-benzylideneamino-2-thiohydantoins (XIII to XVIII). Reaction of the compounds XIX to XXIV with aromatic aldehydes afforded the corresponding hydrazones (XXV to XXVIII). Growth-inhibiting action of these 2-thiohydantoins, hydrazides, and hydrazones against tubercle bacilli was examined.