Novel 3‘,6‘-Anhydro and N12,N13-Bridged Glycosylated Fluoroindolo[2,3- a ]carbazoles as Topoisomerase I Inhibitors. Fluorine as a Leaving Group from sp 3 Carbon

Discovery Chemistry, Bristol-Myers Squibb Pharmaceutical Research Institute, 5 Research Parkway, Wallingford, Connecticut 06492, USA.
Organic Letters (Impact Factor: 6.36). 04/2005; 7(7):1271-4. DOI: 10.1021/ol050013n
Source: PubMed


[reaction: see text] Both 6'- and 4'-fluoro-glycosylated indolo[2,3-a]carbazoles are substrates for base-induced loss of fluorine as a leaving group from sp3 carbon. In the case of alpha-N-glycosylated substrate 3, loss of fluorine from the 6'-position leads to 3,6-anhydroglucose analogue 1. A novel N12,N13-bridged sugar analogue 2 results from loss of 4'-fluorine from beta-N-glycosylated analogue 4. Both analogues 1 and 2 display topo I inhibitory potencies similar to camptothecin.

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