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Article

Novel 5′-Norcarbocyclic Pyrimidine Derivatives as Antibacterial Agents

1
Engelhardt Institute of Molecular Biology of the Russian Academy of Sciences, 32 Vavilov St., Moscow 119991, Russia
2
Gause Institute of New Antibiotics, 11 Bol’shaya Pirogovskaya St., Moscow 119021, Russia
3
ImQuest BioSciences, 7340 Executive Way Suite R, Frederick, MD 21704, USA
4
Central Tuberculosis Research Institute, 2 Yauzskaya Alley, Moscow 107564, Russia
5
Department of Chemistry & Biochemistry, University of Maryland, 1000 Hilltop Circle, Baltimore, MD 21250, USA
*
Author to whom correspondence should be addressed.
A.L.K. and L.A.A. contributed equally to this work.
Molecules 2018, 23(12), 3069; https://doi.org/10.3390/molecules23123069
Received: 2 October 2018 / Revised: 16 November 2018 / Accepted: 20 November 2018 / Published: 23 November 2018
(This article belongs to the Special Issue Bioactive Nucleosides and Nucleotides)
A series of novel 5′-norcarbocyclic derivatives of 5-alkoxymethyl or 5-alkyltriazolyl-methyl uracil were synthesized and the activity of the compounds evaluated against both Gram-positive and Gram-negative bacteria. The growth of Mycobacterium smegmatis was completely inhibited by the most active compounds at a MIC99 of 67 μg/mL (mc2155) and a MIC99 of 6.7–67 μg/mL (VKPM Ac 1339). Several compounds also showed the ability to inhibit the growth of attenuated strains of Mycobacterium tuberculosis ATCC 25177 (MIC99 28–61 μg/mL) and Mycobacterium bovis ATCC 35737 (MIC99 50–60 μg/mL), as well as two virulent strains of M. tuberculosis; a laboratory strain H37Rv (MIC99 20–50 μg/mL) and a clinical strain with multiple drug resistance MS-115 (MIC99 20–50 μg/mL). Transmission electron microscopy (TEM) evaluation of M. tuberculosis H37Rv bacterial cells treated with one of the compounds demonstrated destruction of the bacterial cell wall, suggesting that the mechanism of action for these compounds may be related to their interactions with bacteria cell walls. View Full-Text
Keywords: 5′-norcarbocyclic nucleosides; Mycobacterium tuberculosis; antibacterial activity; uracil derivatives 5′-norcarbocyclic nucleosides; Mycobacterium tuberculosis; antibacterial activity; uracil derivatives
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MDPI and ACS Style

Khandazhinskaya, A.L.; Alexandrova, L.A.; Matyugina, E.S.; Solyev, P.N.; Efremenkova, O.V.; Buckheit, K.W.; Wilkinson, M.; Buckheit, R.W., Jr.; Chernousova, L.N.; Smirnova, T.G.; Andreevskaya, S.N.; Leonova, O.G.; Popenko, V.I.; Kochetkov, S.N.; Seley-Radtke, K.L. Novel 5′-Norcarbocyclic Pyrimidine Derivatives as Antibacterial Agents. Molecules 2018, 23, 3069. https://doi.org/10.3390/molecules23123069

AMA Style

Khandazhinskaya AL, Alexandrova LA, Matyugina ES, Solyev PN, Efremenkova OV, Buckheit KW, Wilkinson M, Buckheit RW Jr., Chernousova LN, Smirnova TG, Andreevskaya SN, Leonova OG, Popenko VI, Kochetkov SN, Seley-Radtke KL. Novel 5′-Norcarbocyclic Pyrimidine Derivatives as Antibacterial Agents. Molecules. 2018; 23(12):3069. https://doi.org/10.3390/molecules23123069

Chicago/Turabian Style

Khandazhinskaya, Anastasia L.; Alexandrova, Liudmila A.; Matyugina, Elena S.; Solyev, Pavel N.; Efremenkova, Olga V.; Buckheit, Karen W.; Wilkinson, Maggie; Buckheit, Robert W., Jr.; Chernousova, Larisa N.; Smirnova, Tatiana G.; Andreevskaya, Sofya N.; Leonova, Olga G.; Popenko, Vladimir I.; Kochetkov, Sergey N.; Seley-Radtke, Katherine L. 2018. "Novel 5′-Norcarbocyclic Pyrimidine Derivatives as Antibacterial Agents" Molecules 23, no. 12: 3069. https://doi.org/10.3390/molecules23123069

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