SYNTHESIS AND ANTIMICROBIAL ACTIVITY OF PYRIMIDINOPHANES CONTAINING A URACIL MOIETY AND A BRIDGING SULFUR ATOM

Pyrimidinophanes containing one 5(6)-alkylsubstituted uracil moiety and a 10- or 12-methylene bridge including a sulfur atom were synthesized. The bridging S atoms of the macrocycles were converted to sulfonium groups by interaction with para-toluenesulfonate methyl or nonyl esters. The resulting amphiphilic pyrimidinophanes were tested for bacteriostatic and fungistatic activity against Gram-positive and Gram-negative bacteria and fungi. Amphiphilic pyrimidinophanes with 5-decyl-6-methyluracil moieties had high levels of bacteriostatic activity against Gram-positive bacteria. The minimum inhibitory concentration of the macrocycle containing a methyl group in the sulfonium grouping against Staphylococcus aureus was 0.75 mu g/ml. These data are of value in seeking new highly effective antimicrobial agents.