Beilstein J. Org. Chem.2016,12, 2556–2562, doi:10.3762/bjoc.12.250
-amino-3-deazapurine and benzoyl-protected 1-O-acetylribose. The novel path is superior to previously described syntheses in terms of efficacy and ease of laboratory handling.
Keywords: deazapurinenucleoside; nucleosidation; protection groups; ribozymes; Introduction
The synthesis of 3-deazaadenosine
nucleosidation of 4-chloroimidazo[4,5-c]pyridine and 1,2,3,5-tetraacetyl-ß-D-ribofuranose in the presence of chloro acetic acid to yield the corresponding 6-chloro-3-deazapurinenucleoside (Scheme 1) [22]. Subsequent attempts to convert the chlorine atom directly by amination under various conditions failed
, p-toluenesulfonic acid (cat.), melt (160 °C), 5 to 10 min. b) NH3 in ethanol (saturated at −30 °C), 140 °C, 89 h [23] or NH3 (30% aq), 200 °C, 5 d, 80% [24].
Synthesis of tribenzoylated 6-azido-3-deazapurinenucleoside 2. a) LiN3 (1.3 equiv), N,N-dimethylformamide, 120 °C, 18 h, 76%. b) 1-O-Acetyl
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Graphical Abstract
Scheme 1:
Synthesis of c3A described by Rousseau et al. in 1966 [22]. a) 1,2,3,5-Tetraacetyl-ß-D-ribofuranose, ch...
Beilstein J. Org. Chem.2014,10, 1333–1338, doi:10.3762/bjoc.10.135
medicinal chemistry literature reveals >200 publications in the field. Additionally, PreQ0 meets all the criteria dictated by the “2-0” rule of kinase-likeness proposed by Aronov et al. [8]. It is likely that compounds derived from PreQ0 display kinase activity.
7-Deazapurinenucleoside chemistry has been
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Graphical Abstract
Figure 1:
Biosynthetic pathway leading to nucleosides queuosine and archaeosine.