Studies on the Syntheses and Antibacterial Activity of Thiohydantoin Related Compounds. IX. : Syntheses of Thiohydantoic acid hydrazides.

Abstract

In order to examine the antibacterial action of 2-thiohydantoin derivatives possessing-NH-CS-NH-group on tubercle bacilli, following synthesis was carried out. Thiohydantoic acid hydrazide (III) was obtained in a good yield by the reaction of 2-thiohydantoin (II) or related compounds with hydrazine hydrate. Heating of III in acetic anhydride resulted in cyclization of 1-acetyl-2-thiohydantoin (I). Condensation of III with various aromatic aldehydes gave various hydrazones. Reaction of II with phenylhydrazine or isonicotinic acid hydrazide gave 1-(4-thiohydantoinyl)-2-phenylhydrazine (XXVI) or 1-(4-thiohydantoinyl)-2-isonicotinoyl hydrazine (XXVII). XXVI and XXVII liberated II on being heated with hydrochloric acid. Growth-inhibiting action of these compounds on tubercle bacilli was examined.