A facile synthesis of 4'-thio-arabinonucleosides as potential antiviral agents from D-glucose. 1995

Y Yoshimura, and M Watanabe, and S Sakata, and N Ashida, and S Miyazaki, and H Machida, and A Matsuda
Research and Development Division, Yamasa Corporation, Chiba, Japan.

As potential antiviral agents, 4'-thio-arabinonucleosides were synthesized. Methyl 3-O-benzyl-xylo-furanoside, readily obtained from D-glucose, was converted to 1,4-anhydro-4-deoxy-4-thio-arabinitol. The protection of hydroxyl groups and the Pummerer rearrangement, followed by Lewis acid induced glycosylation afforded 4'-thio-arabinonucleosides. The compounds showed anti HSV-1 activity.

UI MeSH Term Description Entries
D006031 Glycosylation The synthetic chemistry reaction or enzymatic reaction of adding carbohydrate or glycosyl groups. GLYCOSYLTRANSFERASES carry out the enzymatic glycosylation reactions. The spontaneous, non-enzymatic attachment of reducing sugars to free amino groups in proteins, lipids, or nucleic acids is called GLYCATION (see MAILLARD REACTION). Protein Glycosylation,Glycosylation, Protein
D000998 Antiviral Agents Agents used in the prophylaxis or therapy of VIRUS DISEASES. Some of the ways they may act include preventing viral replication by inhibiting viral DNA polymerase; binding to specific cell-surface receptors and inhibiting viral penetration or uncoating; inhibiting viral protein synthesis; or blocking late stages of virus assembly. Antiviral,Antiviral Agent,Antiviral Drug,Antivirals,Antiviral Drugs,Agent, Antiviral,Agents, Antiviral,Drug, Antiviral,Drugs, Antiviral
D001087 Arabinonucleosides Nucleosides containing arabinose as their sugar moiety. Arabinofuranosylnucleosides
D013872 Thionucleosides Nucleosides in which the base moiety is substituted with one or more sulfur atoms.
D014645 Herpesvirus 3, Human The type species of VARICELLOVIRUS causing CHICKENPOX (varicella) and HERPES ZOSTER (shingles) in humans. Chickenpox Virus,Herpes zoster Virus,Ocular Herpes zoster Virus,VZ Virus,Varicella-Zoster Virus,HHV-3,Herpesvirus 3 (alpha), Human,Herpesvirus Varicellae,Human Herpesvirus 3,Chickenpox Viruses,Herpes zoster Viruses,VZ Viruses,Varicella Zoster Virus,Varicella-Zoster Viruses,Varicellae, Herpesvirus
D015195 Drug Design The molecular designing of drugs for specific purposes (such as DNA-binding, enzyme inhibition, anti-cancer efficacy, etc.) based on knowledge of molecular properties such as activity of functional groups, molecular geometry, and electronic structure, and also on information cataloged on analogous molecules. Drug design is generally computer-assisted molecular modeling and does not include PHARMACOKINETICS, dosage analysis, or drug administration analysis. Computer-Aided Drug Design,Computerized Drug Design,Drug Modeling,Pharmaceutical Design,Computer Aided Drug Design,Computer-Aided Drug Designs,Computerized Drug Designs,Design, Pharmaceutical,Drug Design, Computer-Aided,Drug Design, Computerized,Drug Designs,Drug Modelings,Pharmaceutical Designs
D015394 Molecular Structure The location of the atoms, groups or ions relative to one another in a molecule, as well as the number, type and location of covalent bonds. Structure, Molecular,Molecular Structures,Structures, Molecular
D018258 Herpesvirus 2, Human A species of SIMPLEXVIRUS associated with genital infections (HERPES GENITALIS). It is transmitted by sexual intercourse and close personal contact. HSV-2,Herpes Simplex Virus 2,Human Herpesvirus 2,HHV-2,Herpes Simplex Virus Type 2,Herpesvirus 2 (alpha), Human
D018259 Herpesvirus 1, Human The type species of SIMPLEXVIRUS causing most forms of non-genital herpes simplex in humans. Primary infection occurs mainly in infants and young children and then the virus becomes latent in the dorsal root ganglion. It then is periodically reactivated throughout life causing mostly benign conditions. HSV-1,Herpes Simplex Virus 1,HHV-1,Herpes Simplex Virus Type 1,Herpesvirus 1 (alpha), Human,Human Herpesvirus 1

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