52523-22-5Relevant articles and documents
Furanose-Pyranose Isomerization of Reduced Pyrimidine and Cyclic Urea Ribosides
Kelley, James A.,Driscoll, John S.,McCormack, John J.,Roth, Jeri S.,Marquez, Victor E.
, p. 2351 - 2358 (1986)
Tetrahydrouridine (THU, 2) and other fully reduced cyclic urea ribofuranosyl nucleosides undergo a rapid, acid-catalyzed isomerization to their more stable ribopyranosyl form.This isomerization is characterized by a change in spectral properties and by a greater than 10-fold decrease in potency for those nucleosides that act as potent inhibitors of cytidine deaminase in their ribofuranose form. 1-(β-D-Ribopyranosyl)hexahydropyrimidin-2-one (7) was synthesized and used in conjuction with its furanose isomer 6 as a model compound for more extensive 1H and 13C NMR, mass spectral, and kinetic studies of this isomerization.The 0.4 δ upfield shift and 4-Hz increase 1H in the J1',2' coupling constant for the pyranose anomeric proton in the 1H NMR spectrum is indicative of a pyranose β-CI conformation in which the aglycon and C-2' and C-4' hydroxyls are equatorial.The mass spectra of trimethylsilylated pyranose nucleosides also show a characteristic large shift in the m/z 204-217 abundance and the appearance of two new rearrangement ions at M - 133 and M - 206.For furanose 6 the rate of isomerization is pH and temperature dependent with pyranose 7 predominating by a factor of 6-9 at equilibrium.At pH 1 and 37 deg C, furanose 6 has an initial half-life of less than 12 min.Accordingly, this isomerization may explain the observed lack of enhanced ara-C levels in studies evaluating the oral administration of an ara-C and THU combination to species with an acidic stomach content.
Efficient synthesis of 2′-deoxyzebularine and its α-anomer by the silyl method of N-glycosylation. Crystal structures and conformational study in solution
Ebenryter-Olbinska, Katarzyna,Karolak-Wojciechowska, Janina,Sochacka, Elzbieta
, p. 7 - 15 (2014/05/20)
2′-Deoxyzebularine and its α-anomer have been efficiently synthesized with relatively high stereoselectivity by a modified procedure of the silyl method of the N-glycosidic bond formation. An SnCl4- catalyzed condensation of silylated pyrimidin
FLUORINATED PYRIMIDINE ANALOGS AND METHODS OF USE THEREOF
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Page/Page column 15-16, (2014/09/29)
Fluorinated pyrimidine analog compounds, compositions that include the fluorinated pyrimidine analog compounds, methods for making the fluorinated pyrimidine analog compounds, and methods for inhibiting DNA methyltransferase, treating solid tumors, and treating hematologic cancers by administering the fluorinated pyrimidine analog compounds.