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 beta-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 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.
D000818:Animals; D001562:Benzimidazoles / Q000494:pharmacology*; D055598:Chemical Phenomena; D002621:Chemistry; D003864:Depression, Chemical; D004004:Dichlororibofuranosylbenzimidazole / Q000138:chemical synthesis*; D006027:Glycosides / Q000138:chemical synthesis; D009682:Magnetic Resonance Spectroscopy; D008968:Molecular Conformation; D012332:RNA, Heterogeneous Nuclear / Q000096:biosynthesis*; D012263:Ribonucleosides / Q000138:chemical synthesis*; D013056:Spectrophotometry, Ultraviolet; D013237:Stereoisomerism
D001562:Benzimidazoles; D006027:Glycosides; D012332:RNA, Heterogeneous Nuclear; D012263:Ribonucleosides; D004004:Dichlororibofuranosylbenzimidazole