131-06-6Relevant articles and documents
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Reist et al.
, p. 2208 (1961)
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Synthesis of O2,2′-cyclo-β-D-arabinofuranosyl- and β-D-arabinofuranosyl-5-fluorocytosine
Kvasyuk,Mikhailopulo,Barwolff,Cech
, p. 533 - 536 (1982)
Methods for the synthesis of 5-fluorocytosine by direct fluorination of cytidine tetraacetate with elementary fluorine in acetic acid and by amination of 5-fluorouridine triacetate by the action of sodium hydride and p-toluenesulfonyl chloride and subsequent ammonolysis were studied. 5-Fluorocytidine was converted to O2, 2′-cyclo-β-D-arabinofuranosyl-5-fluorocytosine by the successive action of acetylsalicylyl chloride and acetyl chloride in methanol to remove the protective groups. Removal of the protective groups by means of a methanol solution of ammonia gave β-D-arabinofuranosyl-5-fluorocytosine. The latter was also obtained by amination of β-D-arabinofuranosyl-5-fluorouracil tribenzoate.
Synthesis and anti-viral activity of a series of D- and l-2′-deoxy-2′-fluororibonucleosides in the subgenomic HCV replicon system
Shi, Junxing,Du, Jinfa,Ma, Tianwei,Pankiewicz, Krzysztof W.,Patterson, Steven E.,Tharnish, Phillip M.,McBrayer, Tamara R.,Stuyver, Lieven J.,Otto, Michael J.,Chu, Chung K.,Schinazi, Raymond F.,Watanabe, Kyoichi A.
, p. 1641 - 1652 (2007/10/03)
Based on the discovery of (2′R)-D-2′-deoxy-2′- fluorocytidine as a potent anti-hepatitis C virus (HCV) agent, a series of D- and L-2′-deoxy-2′-fluororibonucleosides with modifications at 5- and/or 4-positions were synthesized and evaluated for their in vitro activity against HCV and bovine viral diarrhea virus (BVDV). The key step in the synthesis, the introduction of 2′-fluoro group, was achieved by either fluorination of 2,2′-anhydronucleosides with hydrogen fluoride-pyridine or potassium fluoride, or a fluorination of arabinonucleosides with DAST. Among the 27 analogues synthesized, only the 5-fluoro compound, namely (2′R)-D-2′-deoxy-2′,5-difluorocytidine (13), demonstrated potent anti-HCV activity and toxicity to ribosomal RNA. The replacement of the 4-amino group with a thiol group resulted in the loss of activity, while the 4-methylthio substituted analogue (25) exhibited inhibition of ribosomal RNA. As N4-hydroxycytidine (NHC) had previously shown potent anti-HCV activity, we combined the two functionalities of the N4-hydroxyl and the 2′-fluoro into one molecule, resulting (2′R)-D-2′-deoxy- 2′-fluoro-N4-hydroxycytidine (23). However, this nucleoside showed neither anti-HCV activity nor toxicity. All the L-forms of the analogues were devoid of anti-HCV activity. None of the compounds showed anti-BVDV activity, suggesting that the BVDV system cannot always predict anti-HCV activity.
A stereospecific synthesis of L-deoxyribose, L-ribose and L-ribosides
Shi, Zhen-Dan,Yang, Bing-Hui,Wu, Yu-Lin
, p. 3287 - 3296 (2007/10/03)
Using an inexpensive D-galactose from the chiral pool, L-deoxyribose, L-ribose and their derivatives were synthesized via mild reaction conditions. During the synthesis of L-deoxyribose, the key deoxygenation of the 2-hydroxy group of 3,5-O-dibenzyl-methyl-L-arabinofuranoside was performed by reduction of the corresponding triflate with tetrabutylammonium borohydride in high yield. During the synthesis of L-ribose, the key step of inversion of the 2-hydroxy group in the same substrate was carried out by intramolecular SN2 tandem reaction. Then the L-ribosyl donors were submitted to glycosidations according to Vorbrüggen's conditions to give L-ribosides (L-uridine, L-5-fluorouridine, L-iodouridine, L-thymidine, L-puridine, L-adenosine and L-guanosine) in excellent yields.
