74580-99-7Relevant academic research and scientific papers
Nucleosides. 116. 1-(β-D-Xylofuranosyl)-5-fluorocytosines with a Leaving Group on the 3' Position. Potential Double-Barreled Masked Precursors of Anticancer Nucleosides
Watanabe, K. A.,Reichman, U.,Chu, C. K.,Hollenberg, D. H.,Fox, J. J.
, p. 1088 - 1094 (2007/10/02)
Syntheses of five pairs of cytosine and 5-fluorocytosine xylofuranosyl nucleosides in which the 3'-hydroxyl group is replaced by Cl, Br, I, OMs, or OTs are described.Those xylosyl nucleosides with a good leaving group at the 3' position exhibit good inhibitory activity against L5178Y and P815 mouse leukemic cells in vitro at rather low concentrations, and like that of ara-C this cytotoxicity is reversed by 2'-deoxycytidine but not by thymidine.Xylosylcytosines are not active against ara-C resistant lines of L5178Y and P815 cells; however the corresponding 5-fluorocytosine analogues exhibit significant cytotoxicity against these ara-C resistant leukemic cell lines, and this activity is reversed by thymidine but not by deoxycytidine.These data support the "double-barreled" masked precursor hypothesis in that xylosyl-5-fluorocytosines substituted at the 3' position by a good leaving group exhibit activity akin to that of ara-C in the ara-C in the ara-C sensitive lines, while these nucleosides act as 5-fluoropyrimidines in the ara-C resistant lines.
