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Stereospecific synthesis by the sodium salt glycosylation method of halogeno benzimidazole 2'-deoxyribose analogues of the inhibitor of hnRNA synthesis, 5,6-dichloro-1-(beta-D-ribofuranosyl)benzimidazole (DRB)

  • The recently developed stereospecific sodium salt glycosylation procedure has been successfully applied to the synthesis of the β-ᴅ-2′-deoxyribofuranosides of benzimidazole, 5,6-dihalogeno benzimidazoles, and some 2-substituted analogues in high yield. The 5,6-dibromo analogue was obtained by bromination of the parent nucleoside. These have all been characterized by spectro­scopic methods, including 1H NMR, which permitted analyses of their solution conformations and comparison with those of the corresponding ribofuranosides. Some biological aspects, including preliminary results on cytotoxicity and antiviral activity, are briefly considered.

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Metadaten
Author:Zygmunt Kazimierczuk, Ryszard StolarskiORCiD, David Shugar
URN:urn:nbn:de:hebis:30:3-817908
DOI:https://doi.org/10.1515/znc-1985-9-1023
ISSN:0939-5075
ISSN:1865-7125
Pubmed Id:https://pubmed.ncbi.nlm.nih.gov/4082730
Parent Title (German):Zeitschrift für Naturforschung, C
Publisher:Verlag der Zeitschrift für Naturforschung
Place of publication:Tübingen
Document Type:Article
Language:English
Date of Publication (online):2014/06/02
Year of first Publication:1985
Publishing Institution:Universitätsbibliothek Johann Christian Senckenberg
Release Date:2024/02/04
Tag:1H NMR; Conformational Properties; Halogenobenzimidazoles; Specific Synthesis; β-ᴅ-2′-Deoxyribosides
Volume:40.1985
Issue:9-10
Page Number:6
First Page:715
Last Page:720
Institutes:Medizin
Biochemie, Chemie und Pharmazie / Biochemie und Chemie
Dewey Decimal Classification:5 Naturwissenschaften und Mathematik / 54 Chemie / 540 Chemie und zugeordnete Wissenschaften
5 Naturwissenschaften und Mathematik / 57 Biowissenschaften; Biologie / 570 Biowissenschaften; Biologie
Sammlungen:Universitätspublikationen
Licence (German):License LogoCreative Commons - Namensnennung-Nicht kommerziell-Keine Bearbeitung 3.0