Synthesis and antibacterial activity of doxycycline neoglycosides.
Basic Information
ID: ALA2417477
Journal: J Nat Prod
Title: Synthesis and antibacterial activity of doxycycline neoglycosides.
Authors: Zhang J, Ponomareva LV, Marchillo K, Zhou M, Andes DR, Thorson JS.
Abstract: A set of 37 doxycycline neoglycosides were prepared, mediated via a C-9 alkoxyamino-glycyl-based spacer reminiscent of that of tigecycline. Subsequent in vitro antibacterial assays against representative drug-resistant Gram negative and Gram positive strains revealed a sugar-dependent activity profile and one doxycycline neoglycoside, the 2'-amino-α-D-glucoside conjugate, to rival that of the parent pharmacophore. In contrast, the representative tetracycline-susceptible strain E. coli 25922 was found to be relatively responsive to a range of doxycycline neoglycosides. This study also extends the use of aminosugars in the context of neoglycosylation via a simple two-step strategy anticipated to be broadly applicable for neoglycorandomization.
CiteXplore: 23987662
DOI: 10.1021/np4003096
Patent ID: ┄