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- Title
Synthesis and antimicrobial activity of pyrimidinophanes with two uracil units and bridging nitrogen atoms.
- Authors
Semenov, V. E.; Voloshina, A. D.; Kulik, N. V.; Uraleva, S. Yu.; Giniyatullin, R. Kh.; Mikhailov, A. S.; Akamsin, V. D.; Efremov, Yu. Ya.; Reznik, V. S.
- Abstract
A series of pyrimidinophanes containing two uracil units and nitrogen atoms in bridging polymethylene chains –(CH2) nN(Et)(CH2) m– ( n, m = 5, 6) have been synthesized. The uracil moieties are represented by 6-methyl-, 5-decyl-6-methyl-, and 5-fluorouracils. Quaternization of the bridging N atom with ethylbromide or n-decylbromide yielded amphiphilic pyrimidinophanes, which were evaluated for their antibacterial and antifungal activity in terms of minimal inhibiting concentration (MIC) against Gram-positive and Gram-negative bacteria and fungi. It has been found that MICs of the amphiphilic pyrimidinophanes decrease with increasing lipophilicity of the alkyl substituents at the bridging N atoms and with increasing polymethylene N(pyr)–N chain length (in some cases MIC against Staphylococcus aureus is below 1 ìg/mL). The MICs increase dramatically upon introduction of lipophilic n-decyl substituents at C(5) atoms of the uracil moiety. The results can be used in the search for new highly effective antimicrobial agents.
- Subjects
PYRIMIDINES; ATOMS; POLYMETHYLENE; DRUG lipophilicity; STAPHYLOCOCCUS; BACTERIA
- Publication
Pharmaceutical Chemistry Journal, 2009, Vol 43, Issue 8, p448
- ISSN
0091-150X
- Publication type
Academic Journal
- DOI
10.1007/s11094-009-0331-y