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Synthesis of Norbornane Bisether Antibiotics via Silver-mediated Alkylation.

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), Escherichia coli (MIC = 8 µg/mL) and methicillin-resistant Staphylococcus aureus (MIC = 8 µg/mL).

SUBMITTER: Hickey SM

PROVIDER: S-EPMC4523246 | biostudies-literature | 2015

REPOSITORIES: biostudies-literature

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Synthesis of Norbornane Bisether Antibiotics via Silver-mediated Alkylation.

Hickey Shane M SM Ashton Trent D TD White Jonathan M JM Li Jian J Nation Roger L RL Yu Heidi Y HY Elliott Alysha G AG Butler Mark S MS Huang Johnny X JX Cooper Matthew A MA Pfeffer Frederick M FM

RSC advances 20150101

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 activ ...[more]

PMID: 26251697

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