Synthesis of certain N-Aryl-N'-(2-pyrimidinyl)guanidine derivatives as potential antimicrobial agents

  • Eisa, H.M. (Department of Medicinal Chemistry, Faculty of Pharmacy, University of Mansoura) ;
  • Tayel, M.A. (Department of Medicinal Chemistry, Faculty of Pharmacy, University of Mansoura) ;
  • Yousif, M.Y. (Department of Medicinal Chemistry, Faculty of Pharmacy, University of Mansoura) ;
  • El-Kerdway, M.M. (Department of Medicinal Chemistry, Faculty of Pharmacy, University of Mansoura)
  • Published : 1990.03.01

Abstract

N-Aryl-N'(4-hydroxy-6-methyl-2-pyrimidinyl)guanidines (IIa-c) were prepared by cyclization of N-arybiguanides (Ia-c) with ethyl acetoacetate. Coupling of compounds (IIa-c) with the appropriate diazotized arylamine gave N-aryl-N'-(5-arylhydrazono-6-methyl-4-oxopyrimidin-2-yl) guanidines (IIIa-f). Whereas, their chlorination with phosphorus oxychloride followed by treatment of N-aryl-N'-(4-Chloro-6-methyl-2-pyrimidinyl)guanidimes (IVac) with the appropriate arylamine afforded the corresponding 4-arylamino derivatives (Vaf). Compounds (IIa-f) were also formed when compounds (1a-c) were treated with ethyl 2-arylhydrazono-3-oxobutyrates. The antimircobial testing of some of the prepared compounds against some pathogenic microorganisms revealed that only two have a marked effect against Escherichia coli.

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