171721-00-9Relevant articles and documents
NOVEL 3′-DEOXY-3′-METHYLIDENE- -L-NUCLEOSIDES
-
, (2011/07/07)
The present invention includes novel 3′-deoxy-3′-methylidene-β-L-nucleosides, pharmaceutical composition comprising such compounds, as well as the methods to treat or to prevent viral infections and in particular HBV and/or HIV infections. In accordance with the present invention, there are provided compounds represented by Formula (I), wherein B is selected from A1 and A2;
Synthesis and Antiviral Activity of 2′-Deoxy-2′-fluoro-L-arabinofuranosyl 1,2,3-Triazole Derivatives
Oelgen, Suereyya,Chu, Chung K.
, p. 804 - 811 (2007/10/03)
The title compounds were prepared by building up the triazole ring at the anomeric position via the glycosyl azides 5 a,b. The anomeric configurations of these nucleosides were assigned by using 1H, 13C and NOESY NMR spectroscopy. Th
Structure-activity relationships of 1-(2-deoxy-2-fluoro-β-L-arabino- furanosyl)pyrimidine nucleosides as anti-hepatitis B virus agents
Ma, Tianwei,Pai, S. Balakrishna,Zhu, Yong Lian,Lin, Ju Sheng,Shanmuganathan, Kirupa,Du, Jinfa,Wang, Chunguang,Kim, Hongbum,Newton, M. Gary,Cheng, Yung Chi,Chu, Chung K.
, p. 2835 - 2843 (2007/10/03)
Since 2'-fluoro-5-methyl-β-L-arabinofuranosyluracil (L-FMAU) has been shown to be a potent anti-HBV agent in vitro, it was of interest to study the structure-activity relationships of related nucleosides. Thus, a series of 1- (2-deoxy-2-fluoro-β-L-arabinofuranosyl)pyrimidine nucleosides have been synthesized and evaluated for antiviral activity against HBV in 2.2.15 cells. For this study, L-ribose was initially used as the starting material. Due to the commercial cost of L-ribose, we have developed an efficient procedure for the preparation of L-ribose derivative 6. Starting from L-xylose, 6 was obtained in an excellent total yield (70%) through the pyridinium dichromate oxidation of the 3-OH group followed by stereoselective reduction with NaBH4. It was further converted to the 1,3,5-tri-O-benzoyl-2-deoxy-2- fluoro-α-L-arabinofuranose (10), which was then condensed with various 5- substituted pyrimidine bases to give the nucleosides. Among the compounds synthesized, the lead compound, L-FMAU (13), exhibited the most potent anti- HBV activity (EC50 0.1 μM). None of the other uracil derivatives showed significant anti-HBV activity up to 10 μM. Among the cytosine analogues, the cytosine (27) and 5-iodocytosine (35) derivatives showed moderately potent anti-HBV activity (EC50 1.4 and 5 μM, respectively). The cytotoxicity of these nucleoside analogues has also been assessed in 2.2.15 cells as well as CEM cells. None of these compounds displayed any toxicity up to 200 μM in 2.2.15 cells. Thus, compound 13 (L-FMAU), 27, and 35 showed a selectivity of over 2000, 140, and 40, respectively.