Add time:08/23/2019         Source:sciencedirect.com

The synthesis and in vitro anti human immunodeficiency virus (HIV) and anti-hepatitis B virus (HBV) activities of some unnatural β-l-nucleoside enantiomers related to the anti-HIV compound 2′,3′-dideoxy-3′-fluoro-5-chlorouridine (β-d-3′Fdd5ClU) are reported. In contrast to β-d-3′Fdd5ClU, β-l-3′Fdd5ClU and the other l-congeners were devoid of significant anti-HIV effects, but β-l-2′,3′-dideoxy-5-chlorocytidine (β-l-dd5ClC) and β-l-2′,3′-dideoxy-3′-fluoro-cytidine (β-l-3′FddC) showed a distinct anti-HBV activity. Three mononucleoside phosphotriester derivatives with S-pivaloyl-2-thioethyl (t-BuSATE) groups as biolabile phosphate protective groups were also synthesized. The bis(t-BuSATE) derivative of β-d-3′Fdd5ClU retained anti-HIV activity in thymidine kinase deficient (TK−) CEM cells.

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