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Title: Synthesis and antimicrobial activity of pyrimidinophanes containing a uracil moiety and a bridging sulfur atom.
Authors: Nikolaev, A.; Semenov, V.; Voloshina, A.; Kulik, N.; Reznik, V.
Abstract: 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 !g/ml. These data are of value in seeking new highly effective antimicrobial agents.
Subjects: URACIL; MACROCYCLIC compounds; SULFONIUM compounds; ANTIBACTERIAL agents; METHYL groups; ANTI-infective agents
Publication: Pharmaceutical Chemistry Journal, 2010, Vol 44, Issue 3, p130
ISSN: 0091-150X
Publication type: Academic Journal
DOI: 10.1007/s11094-010-0414-9

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Synthesis and antimicrobial activity of pyrimidinophanes containing a uracil moiety and a bridging sulfur atom.