862188-13-4Relevant academic research and scientific papers
Catalytic 1,3-Difunctionalization via Oxidative C-C Bond Activation
Banik, Steven M.,Mennie, Katrina M.,Jacobsen, Eric N.
, p. 9152 - 9155 (2017/07/22)
Electronegative substituents arrayed in 1,3-relationships along saturated carbon frameworks can exert strong influence over molecular conformation due to dipole minimization effects. Simple and general methods for incorporation of such functional group relationships could thus provide a valuable tool for modulating molecular shape. Here, we describe a general strategy for the 1,3-oxidation of cyclopropanes using aryl iodine(I-III) catalysis, with emphasis on 1,3-difluorination reactions. These reactions make use of practical, commercially available reagents and can engage a variety of substituted cyclopropane substrates. Analysis of crystal and solution structures of several of the products reveal the consistent effect of 1,3-difluorides in dictating molecular conformation. The generality of the 1,3-oxidation strategy is demonstrated through the catalytic oxidative ring-opening of cyclopropanes for the synthesis of 1,3-fluoroacetoxylated products, 1,3-diols, 1,3-amino alcohols, and 1,3-diamines.
Pradefovir: A prodrug that targets adefovir to the liver for the treatment of hepatitis B
Reddy, K. Raja,Matelich, Michael C.,Ugarkar, Bheemarao G.,Gómez-Galeno, Jorge E.,DaRe, Jay,Ollis, Kristin,Sun, Zhili,Craigo, William,Colby, Timothy J.,Fujitaki, James M.,Boyer, Serge H.,Van Poelje, Paul D.,Erion, Mark D.
, p. 666 - 676 (2008/09/19)
Adefovir dipivoxil, a marketed drug for the treatment of hepatitis B, is dosed at submaximally efficacious doses because of renal toxicity. In an effort to improve the therapeutic index of adefovir, 1-aryl-1,3-propanyl prodrugs were synthesized with the r
