Stereospecific Synthesis by the Sodium Salt Glycosylation Method of Halogeno Benzimidazole 2 -Deoxyribose Analogues of the Inhibitor of hnRNA Synthesis, 5,6-Dichloro-l-(ß-D-ribofuranosyl)benzimidazole (DRB)

Z. Kazimierczuk3, R. Stolarskiab, and D. Shugarae a Department of Biophysics, Institute of Experimental Physics, University of Warsaw, 02-089 Warszawa b Institut für Biophysikalische Chemie, Klinikum der Universität, 6000 Frankfurt am Main 70, GFR c Institute of Biochemistry and Biophysics, Academy of Sciences, 02-532 Warszawa, Poland Z. Naturforsch. 40c, 715-720 (1985); received February 14/May 9, 1985 Halogenobenzimidazoles, ß-D-2'-Deoxyribosides, Specific Synthesis, ‘H NMR, Conformational Properties The recently developed stereospecific sodium salt glycosylation procedure has been successfully applied to the synthesis of the ß-D-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 spectro­ scopic methods, including ‘H 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.