136228-16-5Relevant academic research and scientific papers
The 'β-fluorine effect' in the non-metal hydride radical deoxygenation of fluorine-containing nucleoside xanthates
Siddiqui, Maqbool A.,Driscoll, John S.,Abushanab, Elie,Kelley, James A.,Barchi Jr., Joseph J.,Marquez, Victor E.
, p. 1 - 12 (2007/10/03)
An alternative method to conduct a Barton-McCombie deoxygenation in nucleosides is described. The utility of the procedure is limited to structures with an electronegative substituent, particularly fluorine, in the β-position relative to the radical cente
2'-fluorofuranosyl derivatives and novel method of preparing 2'-fluoropyrimidine and 2'-fluoropurine nucleosides
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, (2008/06/13)
A compound has the formula STR1 wherein R is selected from the group consisting of (C7 -C20)aroyl, (C6 -C20)aryl, aralkyl and alkylaryl, and (C1 -C10)alkyl-di(C6 -C20)aryl Si, R' is selected from the group consisting of (C1 -C10)alkyl, (C7 -C20)aroyl and (C2 -C12)acyl, all of which may be further substituted with O, S, N or alkyl, and R'" is selected from the group consisting of halogen, (C1 -C10)alkoxy, (C1 -C10)acyloxy, O-methane-sulfonyl and O-p-toluenesulfonyl. A composition of matter comprises 0.001 to 99.999 wt % of the above compound.
Chemistry and anti-HIV properties of 2'-fluoro-2',3'- dideoxyarabinofuranosylpyrimidines
Siddiqui,Driscoll,Marquez,Roth,Shirasaka,Mitsuya,Barchi Jr.,Kelley
, p. 2195 - 2201 (2007/10/02)
The synthesis, chemistry, biochemistry, and anti-HIV activity of a series of 1-(2,3-dideoxy-2-fluoro-β-D-threo-pentofuranosyl)pyrimidines have been studied in an attempt to find useful anti-AIDS drugs. Synthesis is carried out via a 2,3-dideoxyribose intermediate which facilitates the preparation of analogues by removing the sugar 3'-hydroxyl group prior to, rather than after, condensation with a uracil or cytosine aglycon. The 2'-F-dd-uridine analogues 7a-d (with H, F, Cl, and CH3 substitution in the 5-position) as well as the 4-deoxy compound (12b) are nonprotective to ATH8 or CEM cells infected with HIV-1. In the corresponding cytidine series, the 5-chloro analogue (11) is inactive. However, 2'-fluoro-2',3'- dideoxyarabinosylcytosine, 10a, and its 5-fluoro analogue, 10b, are both active. While neither compound is as potent as ddC or 5-F-ddC (2b), 10b gives complete protection against the cytopathic effects of HIV in both host cell lines. 2'-Fluoro substitution confers increased chemical and enzymatic stability on dideoxynucleosides. Even though dideoxy pyrimidine nucleosides are inherently more stable than the corresponding purine analogues toward acid-catalyzed cleavage of the glycosidic bond, 2'-fluoro substitution (10a) still increases stabilization relative to ddC (2b). No detectable deamination by partially purified cytidine deaminase is observed with the 2'-fluoro compounds 10a, 10b, or 11 under conditions which rapidly deaminate cytidine. A small amount of 2'-F-dd-ara-U (7a) is formed from 10a in monkey plasma after >24 h of exposure. The octanol-water partition coefficients for the dideoxynucleosides in this study indicate their hydrophilic character, with log P values varying from -0.28 to -1.18.
A more expedient approach to the synthesis of anti-HIV-active 2,3-dideoxy-2-fluoro-β-D-threo-pentofuranosyl nucleosides
Wysocki Jr.,Siddiqui,Barchi Jr.,Driscoll,Marquez
, p. 1005 - 1008 (2007/10/02)
Starting with 1,3,5-tri-O-benzoyl-2-deoxy-2-fluoro-α-D-arabinofuranose, a versatile method for the synthesis of 2,3-dideoxy-2-fluoro-β-D-threo-pentofuranosyl nucleosides is described and illustrated with the synthesis of 9-(2,3-dideoxy-2-fluoro-β-D-threop
