Synthesis of certain 2-aminoadmantane derivatives as potential antimicrobial agents

  • Eisa, Hassan M. (Department of Medicinal Chemistry, Faculty of Pharmacy, University of Mansoura) ;
  • Tantawy, Atif S. (Department of Medicinal Chemistry, Faculty of Pharmacy, University of Mansoura) ;
  • El-Kerdawy, Mohamed-M. (Department of Medicinal Chemistry, Faculty of Pharmacy, University of Mansoura)
  • Published : 1990.03.01

Abstract

N-(2-Amamantyl)-N-(5-arylhydrazono-6-methyl-4-oxopyrimidin-2-yl) guanidines (IIIa, b), 2-(2-admantyl-amino)-4-amino-s-triazine (IVa) and its 6-chloromethyl derivative (IVb) were prepared by cylization of 1-(2-admantyl) biguanide HCl (I) with ethyl 2-arylhydrazono-3-oxobutyrates (II), ethyl formate and ethyl chloroacetate, respectively. Where 1-(2-admantyl)-3-(4, 5-dioxo-2-imidazolidinylidene)guanidine (V) was used as intermediate for the synthesis of amides (VIIa, b), hydrazide (VIII) and azomethine derivatives (IX, b) of alkyl 2-(2-admantyl-amino)-4-amino-2-triazine-6-carboxylates (VI a, b). The antimicrobial testing of the prepared compounds proved that compound 1Xb was the most active. It showed a marked bacteriostatic effect against Staphylococcus aureus and Bacillus subtilis.

Keywords