[Synthesis, conformation analysis, and antiviral activity of benzimidazole ribofuranosides].
To study the structure-biological effect correlation in the series of nucleoside analogues containing deazapurines, a number of 2-R-benzimidazole 1-beta-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 acyclonucleosides, the ribofuranosides obtained are nonactive against entheroviruses and more cytotoxic.
Iavorskiĭ
A E
AE
Turov
A V
AV
Reshot'ko
L N
LN
Florent'ev
V L
VL
D000998:Antiviral Agents / Q000138:chemical synthesis* / Q000737:chemistry; D001562:Benzimidazoles / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D002942:Circular Dichroism; D004578:Electron Spin Resonance Spectroscopy; D008968:Molecular Conformation; D012254:Ribavirin / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D013056:Spectrophotometry, Ultraviolet; D013329:Structure-Activity Relationship
D000998:Antiviral Agents; D001562:Benzimidazoles; D012254:Ribavirin
Sintez, konformatsionnyĭ analiz i izuchenie protivovirusnoĭ aktivnosti ribofuranozidov benzimidazola.