Glycosylation of fluoroquinolones through direct and oxygenated polymethylene linkages as a sugar-mediated active transport system for antimicrobials

…, BT Vu, M Kiankarimi, E Spyrou, J Kaunitz

Index: Jung, Michael E.; Yang, Eric C.; Vu, Binh T.; Kiankarimi, Mehrak; Spyrou, Emmanouil; Kaunitz, Jon Journal of Medicinal Chemistry, 1999 , vol. 42, # 19 p. 3899 - 3909

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Citation Number: 32

Abstract

We report herein the synthesis and biological testing of several glycosylated derivatives of some fluoroquinolone antibiotics. In particular, we have prepared several glycosylated derivatives of ciprofloxacin (2) in which the carbohydrate units are linked to the free secondary amine of the piperazine unit by:(a) no linker (eg, a glycosylamine),(b) a β- oxyethyl linker, and (c) a γ-oxypropyl linker. Both glucose and galactose were used as ...