Novel spironucleosides: 1",3"-thiazolidine-2"-spiro-3'-3'-deoxyuridine derivatives.
Reaction of 2',5'-di-O-TBDMS-3'-ketouridine 1 with L-cysteine yielded in good yield a resolvable mixture of the two expected epimeric spironucleosides 2 and 3. Amidification of their carboxylic group took place readily and the ribo carboxamide 4 was oxidized to the corresponding sulfoxide 6. Despite their similarity to TSAO derivatives these compounds did not exhibit usable anti-HIV activity.
Department of Pharmaceutical Chemistry, Sciences II, University of Geneva, Switzerland.
J M
JM
Tronchet
I
I
Kovács
F
F
Barbalat-Rey
M V
MV
Holm
D019380:Anti-HIV Agents / Q000138:chemical synthesis* / Q000737:chemistry; D003857:Deoxyuridine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D013141:Spiro Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D013844:Thiazoles / Q000138:chemical synthesis / Q000737:chemistry
D019380:Anti-HIV Agents; D013141:Spiro Compounds; D013844:Thiazoles; D003857:Deoxyuridine