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Issue 36, 2015
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Synthesis of norbornane bisether antibiotics via silver-mediated alkylation

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Abstract

A small series of norbornane bisether diguanidines have been synthesized and evaluated as antibacterial agents. The key transformation—bisalkylation of norbornane diol 6—was not successful using Williamson methodology but has been accomplished using Ag2O mediated alkylation. Further functionalization to incorporate two guanidinium groups gave rise to a series of structurally rigid cationic amphiphiles; several of which (16d, 16g and 16h) exhibited antibiotic activity. For example, compound 16d was active against a broad range of bacteria including Pseudomonas aeruginosa (MIC = 8 μg mL−1), Escherichia coli (MIC = 8 μg mL−1) and methicillin-resistant Staphylococcus aureus (MIC = 8 μg mL−1).

Graphical abstract: Synthesis of norbornane bisether antibiotics via silver-mediated alkylation

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Publication details

The article was received on 23 Feb 2015, accepted on 16 Mar 2015 and first published on 16 Mar 2015


Article type: Paper
DOI: 10.1039/C5RA03321G
Citation: RSC Adv., 2015,5, 28582-28596
  • Open access: Creative Commons BY license
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    Synthesis of norbornane bisether antibiotics via silver-mediated alkylation

    S. M. Hickey, T. D. Ashton, J. M. White, J. Li, R. L. Nation, H. Y. Yu, A. G. Elliott, M. S. Butler, J. X. Huang, M. A. Cooper and F. M. Pfeffer, RSC Adv., 2015, 5, 28582
    DOI: 10.1039/C5RA03321G

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