Hydantoin and thiobydantoin derivatives as potential antimicrobial agents II

ABSTRACT

Several hydantoin and 2-thio analog derivatives have been prepared. Condensation of 1,3-dimethyl-1,2,4 imidazolidinedione [IA] and its 2- thio analog [IB] with aromatic aldehydes afforded the corresponding arylidene derivatives. Coupling of [IB] with diazonium salts yielded the expected 5-arylhydrazono derivatives. In addition, reaction of [IB] with formaldehyde and secondary amines gave the expected products. However, attempts to condense [IA] with formaldehyde and secondary amines under the Mannich conditions were abortive, and the same hydantoin failed to couple with aryldiazonium salts. Several trials have been made to prepare a series of 5-hydrazono-1, 3-dimethyl-2,4-imidazolidinediones via desulphurization of the 2-thio analogs, but were unsuccessful. Additionally, the reaction of [IB] with two equivalents of formaldehyde and secondary amines, in the presence of acetic acid, yielded the bis-Mannich bases [IVa and b]. Reaction of [III] with Grignard reagents was studied. Thirteen compounds have been screened against selected bacteria and some of them were found to possess moderate to fairly good antibacterial activity