Synthesis of certain 2-aminoadamantane derivatives as potential antimicrobial agents

ABSTRACT

Several 2-aminoadamantane derivatives that incorporate pyrimidine or s-triazine moiety were synthesized. 2-[2-adamantylguanidino]-5- arylhydrazono-6-methyl-4-pyrimidinone [2a,b], 2-[a-adamantylamino]- 4-amino-s-triazine and its 6-chloromethyl derivative [3a,b] were prepared by cyclization of 1-[2-adamantyl] biguanide HCl [1] with ethyl 2-arylhydrazono-3-oxobutyrates [A], ethyl formate and ethyl chloroacetate, respectively; where 1-[2-adamantyl]-3-[4,5-dioxo-2-imidazoli-dinylidene] guanidine [4] was used as intermediate for the preparation of amides [5a,b], hydrazide [7] and azomethine derivatives [8a,b] of alkyl 2-[2-adamantylamino]-4-amino-s-triazine-6-carboxylates [5a,b]. The antimicrobial testing of the prepared compounds proved that compound [8b] was the most active. It showed a marked bacteriostatic effect against Staphylococcus aureus and Bacillus subtilis