146762-13-2Relevant academic research and scientific papers
Efficient synthesis of 2′-O-alkyl ribonucleosides using trichloroacetimidateDribofuranosides as ribosyl donors
Chanteloup, Luc,Thuong, Nguyen T.
, p. 877 - 880 (1994)
Trichloroacetimidate-2-O-alkyl-3,5-O-TIPS-β- D-ribofuranoside glycosylates silylated nucleobases in a fast high-yielding and stereo selective reaction promoted by trimethylsilyl trifluoromethanesulfonate. This method has been applied to the syn
Asymmetric Synthesis and Biological Evaluation of β-L-(2R,5S)- and α-L-(2R,5R)-1,3-Oxathiolane-Pyrimidine and -Purine Nucleosides as Potential Anti-HIV Agents
Jeong, Lak S.,Shinazi, Raymond F.,Beach, J. Warren,Kim, Hea O.,Nampalli, Satyanarayana,et al.
, p. 181 - 195 (2007/10/02)
In order to study the structure-acivity relationships of L-oxathiolanyl nucleosides as potential anti-HIV agents, a series of enantiomerically pure L-oxathiolanyl pyrimidine and purine nucleosides were synthesized and evaluated for anti-HIV-1 activity in human peripheral blood mononuclear (PBM) cells.The key intermediate 8 was synthesized starting from L-gulose via 1,6-thiaanhydro-L-gulopyranose.The acetate 8 was condensed with thymine, 5-substituted uracils and cytosines, 6-chloropurine, and 6-chloro-2-fluoropurine to give pyrimidine and purine nucleosides.Upon evaluation of these final nucleosides, the 5-fluorocytosine derivative 51 was found to be the most potent compound among those tested.In the case of 5-substituted cytosine analogues, the antiviral potency was found to be in the following decreasing order: cytosine (β-isomer) > 5-iodocytosine (β-isomer) > 5-fluorocytosine (α-isomer) > 5-methylcytosine (α-isomer) > 5-methylcytosine (β-isomer) > 5-bromocytosine (β-isomer) > 5-chlorocytosine (β-isomer).Among the thymine, uracil, and 5-substituted uracil derivatives, thymine (α-isomer) and uracil (β-isomer) derivatives exhibited moderate anti-HIV activity.In the purine series, the antiviral potency is found to be in the following decreasing order: adenine (β-isomer) > 6-chloropurine (β-isomer) > 6-chloropurine (α-isomer) > 2-NH2-6-Cl-purine (β-isomer) > guanine (β-isomer) > N6-methyladenine (α-isomer) > N6-methyladenine (β-isomer).The cytotoxicity was also determined in human PBM cells as well as Vero cells.None of the synthesized nucleosides was toxic up to 100 μ in PBM cells.
Structure-Activity Relationships of β-D-(2S,5R)- and α-D-(2S,5S)-1,3-oxathiolanyl Nucleosides as Potential Anti-HIV Agents
Jeong, Lak S.,Schinazi, Raymond F.,Beach, J. Warren,Kim, Hea O.,Shanmuganathan, Kirupathevy,et al.
, p. 2627 - 2638 (2007/10/02)
The β-D-(2S,5R)- and α-D-(2S,5S)-1,3-oxathiolanylpyrimidine and -purine nucleosides with natural nucleoside configuration were synthesized and evaluated against HIV-1 in human peripheral blood mononuclear (PBM) cells.The key intermediate 14, which was uti
SYNTHESIS OF 2',3'-DIDEOXY-D-ERYTHRO-HEX-2'-ENOPYRANOSYL NUCLEOSIDES FROM 5-AMINOURACILS AND 3,4,6-TRI-O-ACETYL-D-GLUCAL
Pedersen, Henrik,Pedersen, Erik B.,Nielsen, Carsten M.
, p. 265 - 272 (2007/10/02)
Condensation of silylated N,N-disubstituted aminouracils (4) and 3,4,6-tri-O-acetyl-D-glucal (3) in the presence of TMS triflate as catalyst gave anomeric mixtures of 2',3'-dideoxy-D-erythro-hex-2'-enopyranosylnucleosides (5) and (6).The pure β- and α-ano
