29571-45-7Relevant academic research and scientific papers
Synthesis of L-analogues of 1-(2',3'-dideoxy-β-D-glycero-pent-2-enofuranosyl)thymine
Camara,Ciurea,Delbederi,Fossey,Fontaine,Gavriliu,Jouenne,Laduree,Aubertin,Kirn
, p. 225 - 231 (2007/10/03)
β-L(-)-2',3'-Dideoxy-3'-thiacytidine (3TC), its 5-fluoro derivative ((-)-FTC), 2',3'-dideoxycytidine (β-L-ddC), and its 5-fluoro derivative (β-L-FddC) have been reported to have anti-HIV and anti-HBV activity. It was of particular interest therefore to develop a series of β-L-d4T analogues bearing several kinds of amino-linker arms at the C-5 position of the pyrimidine moiety in an attempt to find more potent and less toxic anti-HIV agents. In addition, modification of nucleosides with various functional molecules has been attracting wide interest in biological studies since die primary amino groups could be useful for the attachment of either fluorescent dyes or a non-nucleosidic reverse transcriptase inhibitor. These modified nucleosides were evaluated for antiviral activity against HIV-1(LAI) in CEM-SS cells and HIV-1(IIIB) in MT4 cells. Unfortunately, none of the compounds exhibited significant anti-HIV activity at the doses tested.
An Unusual Substituent Effect on Elimination vs Fragmentation Reactions of the Dianions of 5-Fluorouracil-Alkene Photoadducts. Preparation of Cyclobutane-Annelated Uracils
Swenton, John S.,Jurcak, John G.
, p. 1530 - 1534 (2007/10/02)
Acetone-sensitized photocycloadditions of 5-fluorouracil to methyl vinyl ether, 2-methoxypropene, and ketene dimethyl acetal give good yields of the respective 8,8-disubstituted-6-fluoro-2,4-diazabicyclooctane-3,5-diones.Whereas the dianions of cycloadducts of 5-fluorouracil and alkyl-substituted alkenes afford high yields of 5-substituted uracils, the products from 2-methoxypropene and ketene dimethyl acetal give predominantly cyclobutane-annelated uracils derived from syn elimination of hydrogen fluoride.Deuterium labeling studies support the proposed mechanism of elimination.Heating 8,8-dimethoxy-2,4-diazabicyclooct-1(6)-ene-3,5-dione, obtained from hydrogen fluoride elimination of the 5-fluorouracil-ketene dimethyl acetal photoadduct, in the presence of N-phenylmaleimide or dimethyl acetylenedicarboxylate, gives Diels-Alder adducts derived from trapping the thermally generated diene.
