-transparent.png){kind=logo}
Diazomethane treatment of ribavirin (1-beta-D-ribofuranosyl-1,2,4-triazole-3-carboxamide) in the presence of SnCl2 as catalyst led to quantitative formation of the 2'-O-methyl and 3'-O-methyl derivatives of the parent compound. The products were successfully fractionated on a basic ion-exchange column and isolated in crystalline form. Indentification was based on the elution sequence from the column and on 1H NMR spectroscopy. Both derivatives were found to be inactive, relative to the parent compound, against several virus types in cell culture. Unlike ribavirin itself, the 2'(3')-O-methyl derivatives did not suppress cellular DNA synthesis. NMR data showed that the loss of biologic activity upon 2'(3')-O-methylation was not due to a change of conformation of the nucleoside sugar moiety.
L Dudycz, and
D Shugar, and
E D Clercq, and
J Descamps
March 1977,
Annals of the New York Academy of Sciences,
L Dudycz, and
D Shugar, and
E D Clercq, and
J Descamps
August 1972,
Science (New York, N.Y.),
L Dudycz, and
D Shugar, and
E D Clercq, and
J Descamps
August 1978,
Journal of medicinal chemistry,
L Dudycz, and
D Shugar, and
E D Clercq, and
J Descamps
June 1976,
Journal of medicinal chemistry,
L Dudycz, and
D Shugar, and
E D Clercq, and
J Descamps
January 2000,
Nucleosides, nucleotides & nucleic acids,
L Dudycz, and
D Shugar, and
E D Clercq, and
J Descamps
November 1972,
Journal of medicinal chemistry,
L Dudycz, and
D Shugar, and
E D Clercq, and
J Descamps
June 1977,
Biochemical pharmacology,
L Dudycz, and
D Shugar, and
E D Clercq, and
J Descamps
April 1980,
Immunopharmacology,
L Dudycz, and
D Shugar, and
E D Clercq, and
J Descamps
March 1975,
Proceedings of the Society for Experimental Biology and Medicine. Society for Experimental Biology and Medicine (New York, N.Y.),
L Dudycz, and
D Shugar, and
E D Clercq, and
J Descamps
August 1976,
The Journal of general virology,
