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2005
Nucleic acids
U 0700
Thiosugar Nucleosides. Synthesis and Biological Activity of 1,3,4-Thiadiazole,
and Thiourea Derivatives of 5-Thio-D-Glucose. — Thiosugars (V) and
20- 206 Thiazoline
(VII) are prepared via spontaneous rearrangement by cycloaddition of glycosyl isothiocyanate (III) with reactive allene salts, generated by reaction of SbCl5 with azo compounds (IV) and (VI), respectively. Reaction of β-haloalkylamine (VIII) with (III) furnishes a foam, tentatively identified as thiazoline derivative (IX). Using chloroethylamine (VIII) and (III) in a 1:2 ratio the thioureylendisaccharide (X) is formed. The
deblocked nucleosides show no antiviral activity against HIV-1, HIV-2, and human
cytomegalovirus (HMCV). — (AL-MASOUDI*, N. A.; AL-SOUD, Y. A.;
AL-MASOUDI, W. A.; Nucleosides, Nucleotides Nucleic Acids 23 (2004) 11,
1739-1749; Fak. Chem., Univ. Konstanz, D-78434 Konstanz, Germany; Eng.) —
H. Hoennerscheid
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