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Synthesis of norbornane bisether antibiotics via silver-mediated alkylation

Hickey, Shane M., Ashton, Trent D., White, Jonathan M., Li, Jian, Nation, Roger L., Yu, Heidi Y., Elliott, Alysha G., Butler, Mark S., Huang, Johnny X., Cooper, Matthew A. and Pfeffer, Frederick M. 2015, Synthesis of norbornane bisether antibiotics via silver-mediated alkylation, RSC advances, vol. 5, no. 36, pp. 28582-28596, doi: 10.1039/C5RA03321G.

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Title Synthesis of norbornane bisether antibiotics via silver-mediated alkylation
Author(s) Hickey, Shane M.
Ashton, Trent D.ORCID iD for Ashton, Trent D. orcid.org/0000-0002-6707-6064
White, Jonathan M.
Li, Jian
Nation, Roger L.
Yu, Heidi Y.
Elliott, Alysha G.
Butler, Mark S.
Huang, Johnny X.
Cooper, Matthew A.
Pfeffer, Frederick M.ORCID iD for Pfeffer, Frederick M. orcid.org/0000-0002-5441-6437
Journal name RSC advances
Volume number 5
Issue number 36
Start page 28582
End page 28596
Total pages 15
Publisher Royal Society of Chemistry
Place of publication London, Eng.
Publication date 2015
ISSN 2046-2069
Keyword(s) Science & Technology
Physical Sciences
Chemistry, Multidisciplinary
Chemistry
INFECTIOUS-DISEASES-SOCIETY
ADENOSINE AGONISTS
DRUG DISCOVERY
BAD BUGS
FRAGMENTATION
PIPELINE
ROUTE
HOSTS
TOPOMIMETICS
DERIVATIVES
Summary 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), Escherichia coli (MIC = 8 µg/mL) and methicillin-resistant Staphylococcus aureus (MIC = 8 µg/mL).
Language eng
DOI 10.1039/C5RA03321G
Field of Research 030503 Organic Chemical Synthesis
030401 Biologically Active Molecules
030302 Nanochemistry and Supramolecular Chemistry
Socio Economic Objective 970103 Expanding Knowledge in the Chemical Sciences
HERDC Research category C1 Refereed article in a scholarly journal
ERA Research output type C Journal article
Copyright notice ©2015, The Authors
Free to Read? Yes
Use Rights Creative Commons Attribution licence
Persistent URL http://hdl.handle.net/10536/DRO/DU:30076866

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Every reasonable effort has been made to ensure that permission has been obtained for items included in DRO. If you believe that your rights have been infringed by this repository, please contact drosupport@deakin.edu.au.