178374-44-2Relevant articles and documents
Synthesis of 3′-Deoxy-3′-fluoro and -3′-amino Nucleosides from 2-Methylthiopyrimidin-4(1H)-ones
Zahran,Abdel-Megied,Abdel-Rahman,Sofan,Nielsen,Pedersen
, p. 979 - 988 (1996)
Methyl 2,3-dideoxy-3-fluoro-5-O-(4-phenylbenzoyl)-β-D-erythro-pentofuranoside (3) as well as 1,5-di-O-acetyl-2,3-dideoxy-3-phthalimodo-β-D-erythro-pentofuranose (12) were condensed with silylated 2-methylthiopyridin-4(1H)-ones 2a, b in the presence of trimethylsilyl triflate as a catalyst to produce the corresponding nucleosides 5, 6, 13. In these reactions, an endocyclic cleavage of C-O in 3 took place; therefore, acyclic nucleosides 4a, b were also formed. All 3′-fluoro nucleosides were deprotected with NH3/MeOH; the 3′-phthalimido nucleosides were deprotected with methylamine in ethanol. The latter method resulted in a concomitant substitution reaction in the pyrimidine moiety with replacement of the methylthio group. The 2-methylthio analogue of 3′-deoxy-3′-fluorothylmidine showed moderate activity against HIV-1.
Newly synthesized L-enantiomers of 3'-fluoro-modified β-2'- deoxyribonucleoside 5'-triphosphates inhibit hepatitis B DNA polymerases but not the five cellular DNA polymerases α, β, Γ, δ, and ε nor HIV-1 reverse transcriptase
Von Janta-Lipinski, Martin,Costisella, Burkhardt,Ochs, Hansueli,Hübscher, Ulrich,Hafkemeyer, Peter,Matthes, Eckart
, p. 2040 - 2046 (2007/10/03)
Novel β-L-2',3'-dideoxy-3'-fluoro nucleosides were synthesized and further converted to their 5'-triphosphates. Their inhibitory activities against hepatitis B virus (HBV) and duck hepatitis B virus (DHBV) DNA polymerases, α, ?, γ, δ and ε were investigat
Antiviral agents
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, (2008/06/13)
Nucleoside compounds of the formula STR1 wherein: B is a purine or a pyrimidine; X and X' are H, OH or F, provided that at least one is H; Y and Y' are H, OH, OCH3 or F, provided that at least one is H; Y' and Z together form a cyclic phosphate ester, provided that Y is H; or Z is STR2 where n is zero, one, two or three; and Z' is N3 or OCH3 ; provided that when X' and Y' are OH and Z' is N3, B is not cytosine, and when X' and Y' are OH and Z' is OCH3, B is not uracil, adenine or cytosine; and the pharmaceutically acceptable esters, ethers and salts thereof, have been found to have potent antiviral activity with a high therapeutic ratio.
