Synthesis of Enantiomerically Pure (S)-Methanocarbaribo Uracil Nucleoside Derivatives for Use as Antiviral Agents and P2Y Receptor Ligands
- 24 September 2008
- journal article
- research article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 73 (20) , 8085-8088
- https://doi.org/10.1021/jo801224j
Abstract
We have developed an approach toward enantiomerically pure (S)-methanocarba ribonucleosides based on several functional group transformations on a sensitive bicyclo[3.1.0]hexane system. d-Ribose was transformed into methanocarba alcohol 3 followed by conversion of the OH group to a nitrile with inversion of configuration at C4. The nitrile group was subsequently reduced in two stages to the 5′-hydroxymethyl group. An ester group appended to a tertiary carbon (C1) was transformed to an amino group as a nucleobase precursor.This publication has 14 references indexed in Scilit:
- Stereoselective Synthesis of 2‘-C-Methyl-cyclopropyl-Fused Carbanucleosides as Potential Anti-HCV AgentsOrganic Letters, 2006
- Human P2Y6 Receptor: Molecular Modeling Leads to the Rational Design of a Novel Agonist Based on a Unique Conformational PreferenceJournal of Medicinal Chemistry, 2005
- MRS2500 [2-Iodo-N6-methyl-(N)-methanocarba-2′-deoxyadenosine-3′,5′-bisphosphate], a Potent, Selective, and Stable Antagonist of the Platelet P2Y1Receptor with Strong Antithrombotic Activity in MiceThe Journal of Pharmacology and Experimental Therapeutics, 2005
- Biochemical and Structural Characterization of (South)-Methanocarbathymidine That Specifically Inhibits Growth of Herpes Simplex Virus Type 1 Thymidine Kinase-transduced Osteosarcoma CellsJournal of Biological Chemistry, 2004
- 2-Substitution of Adenine Nucleotide Analogues Containing a Bicyclo[3.1.0]hexane Ring System Locked in a Northern Conformation: Enhanced Potency as P2Y1Receptor AntagonistsJournal of Medicinal Chemistry, 2003
- Bicyclo[3.1.0]hexanes from sugar-derived diazo compounds and iodonium ylides. Diastereocontrol and synthetic applicationsTetrahedron, 2002
- Methanocarba Modification of Uracil and Adenine Nucleotides: High Potency of Northern Ring Conformation at P2Y1, P2Y2, P2Y4, and P2Y11 but Not P2Y6 ReceptorsJournal of Medicinal Chemistry, 2001
- Synthesis Using Ring Closure Metathesis and Effect on Nucleoside Transport of a (N)-Methanocarba S-(4-Nitrobenzyl)thioinosine DerivativeOrganic Letters, 2001
- Construction of the Bicyclo[3.1.0]hexane Template of a Conformationally Locked Carbocyclic Adenosine via an Olefin Keto-Carbene CycloadditionThe Journal of Organic Chemistry, 2000
- Nucleosides with a Twist. Can Fixed Forms of Sugar Ring Pucker Influence Biological Activity in Nucleosides and Oligonucleotides?Journal of Medicinal Chemistry, 1996