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1-(3-cyano-2,3-dideoxy-beta-D-erythro-pentofuranosyl)thymine (cyanothymidine): synthesis and antiviral evaluation against human immunodeficiency virus. 1989
C W Greengrass, and
D W Hoople, and
S D Street, and
F Hamilton, and
M S Marriott, and
J Bordner, and
A G Dalgleish, and
H Mitsuya, and
S Broder
Pfizer Central Research, Sandwich, Kent, United Kingdom.
1-(3-Cyano-2,3-dideoxy-beta-D-erythro-pentofuranosyl)thymine (cyanothymidine) (3a) has been prepared by an unambiguous route starting from D-xylose. The relative and absolute stereochemistry of 3a and its anomeric isomer 9 have been confirmed by NOE experiments and by X-ray diffraction analysis. In antiviral tests vs HIV 3a was shown to be inactive, a surprising result in view of a preliminary disclosure claiming potent anti-HIV activity. The activity previously assigned to 3a is believed to be due to contamination of that sample with the known antiviral nucleoside analogue 5b.
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S Broder
September 1991,
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H Mitsuya, and
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December 1988,
Carbohydrate research,
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M S Marriott, and
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H Mitsuya, and
S Broder
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Bioorganic & medicinal chemistry,
C W Greengrass, and
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S D Street, and
F Hamilton, and
M S Marriott, and
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A G Dalgleish, and
H Mitsuya, and
S Broder
January 2001,
Nucleosides, nucleotides & nucleic acids,
C W Greengrass, and
D W Hoople, and
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F Hamilton, and
M S Marriott, and
J Bordner, and
A G Dalgleish, and
H Mitsuya, and
S Broder
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Journal of medicinal chemistry,
C W Greengrass, and
D W Hoople, and
S D Street, and
F Hamilton, and
M S Marriott, and
J Bordner, and
A G Dalgleish, and
H Mitsuya, and
S Broder
October 1991,
Acta chemica Scandinavica (Copenhagen, Denmark : 1989),
C W Greengrass, and
D W Hoople, and
S D Street, and
F Hamilton, and
M S Marriott, and
J Bordner, and
A G Dalgleish, and
H Mitsuya, and
S Broder
August 1973,
Carbohydrate research,
C W Greengrass, and
D W Hoople, and
S D Street, and
F Hamilton, and
M S Marriott, and
J Bordner, and
A G Dalgleish, and
H Mitsuya, and
S Broder
April 1968,
The Journal of organic chemistry,
C W Greengrass, and
D W Hoople, and
S D Street, and
F Hamilton, and
M S Marriott, and
J Bordner, and
A G Dalgleish, and
H Mitsuya, and
S Broder
November 2001,
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