Synthesis of certain 2-aminoadamantane derivatives as potential antimicrobial agents.
1-(2-Adamantyl-3-(5-arylhydrazono-6-methyl-4-oxopyrimidin -2-yl)guanidines, 2-(2-adamantylamino)-4-amino-s-triazine and its 6-chloromethyl derivative were prepared by cyclization of 1-(2-adamantyl)biguanide.HCl with ethyl 2-arylhydrazono-3-oxobutyrates, ethyl formate and ethyl chloroacetate, respectively. 1-(2-damantyl)-3-(4,5-dioxo-2-imidazolidinylidene)guanidine was used as intermediate for the synthesis of amides, hydrazide and azomethine derivatives of alkyl 2-(2-adamantylamino)-4-amino-s-triazine-6-carboxylates. The antimicrobial testing of the prepared compounds proved that an azomethine derivative was the most active. It showed a marked bacteriostatic effect against Staphylococcus aureus and Bacillus subtilis.
Eisa
H M
HM
Department of Medicinal Chemistry, Faculty of Pharmacy, University of Mansoura, Egypt.
Tantawy
A S
AS
el-Kerdawy
M M
MM
D000218:Adamantane / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000494:pharmacology; D000900:Anti-Bacterial Agents / Q000138:chemical synthesis*; D001412:Bacillus subtilis / Q000187:drug effects; D001419:Bacteria / Q000187:drug effects*; D004926:Escherichia coli / Q000187:drug effects; D006146:Guanidines / Q000138:chemical synthesis* / Q000494:pharmacology; D008826:Microbial Sensitivity Tests; D013211:Staphylococcus aureus / Q000187:drug effects; D014227:Triazines / Q000138:chemical synthesis* / Q000494:pharmacology
D000900:Anti-Bacterial Agents; D006146:Guanidines; D014227:Triazines; D000218:Adamantane