-transparent.png){kind=logo}
The syntheses of several 2'-halogeno-5-substituted-arabinofuranosylcytosines and -uracils are described, and relationships of structure to anti herpes virus activity in vitro were examined. Those arabinonucleosides containing the 2'-fluoro function exhibit, generally, more potent anti herpes virus (HSV) activity than do their 2'-chloro of 2'-bromo analogues. The importance of the fluorine in the 2'-"up" (arabino) configuration for enhancement of antiviral effectiveness is demonstrated by the superior activity of 2'-fluoro-5-iodo-ara-C [3a, FIAC] to that of 2'-fluoro-5-iodo-ribo-C. Of all the nucleosides tested herein, FIAC exhibited the most potent in vitro activity against HSV. 2'-Chloro-5-iodo- and -5-methyl-ara-C (3b and 4b) were 37 to greater than 500 times more effective in vitro against HSV type 2 than against type 1, suggesting that these latter derivatives might serve clinically as useful probes to distinguish between HSV types 1 and 2 in the diagnosis of HSV infections in man.
K A Watanabe, and
T L Su, and
R S Klein, and
C K Chu, and
A Matsuda, and
M W Chun, and
C Lopez, and
J J Fox
June 1985,
Journal of medicinal chemistry,
K A Watanabe, and
T L Su, and
R S Klein, and
C K Chu, and
A Matsuda, and
M W Chun, and
C Lopez, and
J J Fox
February 1975,
Carbohydrate research,
K A Watanabe, and
T L Su, and
R S Klein, and
C K Chu, and
A Matsuda, and
M W Chun, and
C Lopez, and
J J Fox
January 1990,
Journal of medicinal chemistry,
K A Watanabe, and
T L Su, and
R S Klein, and
C K Chu, and
A Matsuda, and
M W Chun, and
C Lopez, and
J J Fox
November 1987,
Chemical & pharmaceutical bulletin,
K A Watanabe, and
T L Su, and
R S Klein, and
C K Chu, and
A Matsuda, and
M W Chun, and
C Lopez, and
J J Fox
December 1987,
Journal of medicinal chemistry,
K A Watanabe, and
T L Su, and
R S Klein, and
C K Chu, and
A Matsuda, and
M W Chun, and
C Lopez, and
J J Fox
March 1979,
Chemical & pharmaceutical bulletin,
K A Watanabe, and
T L Su, and
R S Klein, and
C K Chu, and
A Matsuda, and
M W Chun, and
C Lopez, and
J J Fox
June 1979,
Journal of medicinal chemistry,
K A Watanabe, and
T L Su, and
R S Klein, and
C K Chu, and
A Matsuda, and
M W Chun, and
C Lopez, and
J J Fox
January 1998,
Nucleosides & nucleotides,
K A Watanabe, and
T L Su, and
R S Klein, and
C K Chu, and
A Matsuda, and
M W Chun, and
C Lopez, and
J J Fox
December 1993,
Journal of medicinal chemistry,
K A Watanabe, and
T L Su, and
R S Klein, and
C K Chu, and
A Matsuda, and
M W Chun, and
C Lopez, and
J J Fox
January 1999,
Nucleosides & nucleotides,
