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.
Author: | Zygmunt Kazimierczuk, Ryszard StolarskiORCiD, David Shugar |
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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): | Creative Commons - Namensnennung-Nicht kommerziell-Keine Bearbeitung 3.0 |