On the basis of potent biological activity of 3'-branched-3'-deoxynucleoside analogues, novel ribavirin and tiazofurin derivatives with 3'-C-hydroxymethyl substituent were synthesized, starting from D-xylose.
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A Galactoside-Binding Protein Tricked into Binding Unnatural Pyranose Derivatives: 3-Deoxy-3-Methyl-Gulosides Selectively Inhibit Galectin-1.
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Centre for Analysis and Synthesis, Department of Chemistry, Lund University, Box 124, SE-221 00 Lund, Sweden.
Galectins are a family of galactoside-recognizing proteins involved in different galectin-subtype-specific inflammatory and tumor-promoting processes, which motivates the development of inhibitors that are more selective galectin inhibitors than natural ligand fragments. Here, we describe the synthesis and evaluation of 3--methyl-gulopyranoside derivatives and their evaluation as galectin inhibitors. Methyl 3-deoxy-3--(hydroxymethyl)-β-d-gulopyranoside showed 7-fold better affinity for galectin-1 than the natural monosaccharide fragment analog methyl β-d-galactopyranoside, as well as a high selectivity over galectin-2, 3, 4, 7, 8, and 9.
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Idenix Pharmaceuticals, 320 Bent Street, Cambridge, Massachusetts 02141, United States.
The synthesis of the novel 2',3'-cyclopropane nucleoside 3'-deoxy-3'-C-hydroxymethyl-2',3'-methylene-uridine is described. Stereoselective construction of the cyclopropane ring was achieved via Simmons-Smith cyclopropanation of a benzyl protected silyl enol ether, which was itself derived from 1,2-O-isopropylidene-α-D-xylofuranose.
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Nucleosides Nucleotides Nucleic Acids
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Research Institute of Pharmaceutical Sciences, College of Pharmacy, Seoul National University, Seoul 151-742, Korea.
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A versatile solid phase combinatorial approach was developed and utilized for the rapid synthesis of new 2'-O-methylcytidine nucleoside libraries 1-7 containing 672 compounds with 3'-deoxy-3'-C-methyl, 3'-deoxy-3'-C-hydroxymethyl, and 5-alkyl/alkynyl modifications. The modified uridine scaffolds 8-10, 23-25, and 31 were loaded onto the 4-methoxytrityl chloride (MMT-Cl) polystyrene resin through the hydroxyl groups at the 5'-position as well as on the substituents at the 3'- and 5-positions. The scaffolds loaded on the resin were orthogonally protected by MMT group on the resin itself and TBDMS or acetyl protecting groups.
View Article and Find Full Text PDFSynthesis of novel D- and L-3'-deoxy-3'-C-hydroxymethyl nucleoside with exocyclic methylene as potential ribonucleotide reductase inhibitor.
Nucleosides Nucleotides Nucleic Acids
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College of Pharmacy, Seoul National University, Seoul 151-742, Korea.
D- and L-3'-Deoxy-3'-C-hydroxymethyl thymidine substituted with exocyclic methylene at 2'-position were synthesized, starting from D- and L-xylose as potential ribonucleotide reductase inhibitor, respectively, but they were found to be inactive against several tumor cell lines.
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