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

ArticleinOrganic Letters 7(7):1271-4 · April 2005with4 Reads
Impact Factor: 6.36 · DOI: 10.1021/ol050013n · Source: PubMed

    Abstract

    [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.