Synthesis, conformational analysis and antiviral activity of benzimidazole ribofuranosides

A. E. Yavorsky, A, V. Turov, L. N. Reshotko, V. L. Florentiev

T. G. Shevchenko Kiev State University, Kiev; Ukrainian Research Veterinary Institute, Kiev: V. A. Engelhardt Institute of Molecular Biology, Academy of Sciences of the USSR, Moscow

Abstract: To study the structure-biological effect correlation in the series of nucleoside analogues containing deazapurines, a number of 2-R-benzimidazole l-β-D-ribofuranosides (R=H, CF3, SCF3, CH2SCF3, CH2Ph, CH2CN) have been prepared by the modified silyl method. On the basis of CD and PMR data it was shown that the compounds exist in solution mainly as syn-conformers. Calculation of the furanose ring pseudorotation parameters in terms of N-S model indicates the predominance of S-population. In contrast to acyclonucleosjdes, the ribofuranosides obtained are nonactive against entheroviruses and more cytotoxic.

Russian Journal of Bioorganic Chemistry 1990, 16 (7):963-968

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