33399-91-6Relevant articles and documents
Synthesis and antimicrobial activity of novel 3- [(aminopyrimidiniumyl)thio]methyl cephalosporins
Kim,Lim,Yeo,Bang,Kim,Kim,Woo -,Yang,Oh,Nahm
, p. 3828 - 3833 (2007/10/02)
A series of novel cephalosporin compounds which have 3- [(aminopyrimidiniumyl)thio]methyl substituents was synthesized. They show high antimicrobial activity against various bacterial species including Pseudomonas aeruginosa. Structure-activity relationships with various thiopyrimidines, thiopyrimidiniums, bicyclic thiotriazolopyrimidiniums, and bicyclic thioimidazolopyrimidiniums as 3'-substituents were also studied; cephalosporins with quarternized pyrimidinium moieties have better antimicrobial activities than neuteral pyrimidine cephalosporins, and stabilization of the positive charge on the pyrimidinium moieties is essential for better activity. According to semiempirical PM3 calculations, amino and alkylthio substituents on the pyrimidinium rings play a major role in charge stabilization and delocalization.