ISSN:
0021-8383
Keywords:
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
Synthesis and Biochemical Activity of Perfluoroalkylated Derivatives of 5′-Deoxy-5′-fluoro-, and 2′, 5′-Dideoxy-5′-fluorouridine5-Perfluoroalkylated 5′-deoxy-5′-fluoro-, and 2′,5′-dideoxy-5′-fluorouridine are obtained by the reaction of 5′-fluorouridine or 2′,5′-dideoxy-5′-fluorouridine, respectively, with a perfluoroalkyl-coppercomplex in DMSO under inert conditions, and at temperatures of about 100 °C. Analogously 5-perfluoroethyl, 5-perfluorobutyl, and 5-perfluorohexyl derivatives of uridine, and 5-perfluoroethyl, and 5-perfluorobutyl derivatives of 2′-deoxyuridine could be isolated. It is shown either by mass spectroscopy or by 1H-n.m.r. spectroscopy that the substitution always takes place at the 5-position of the pyrimidine. The 5-perfluoroethyl derivatives are particularly effective as cytostatics.
Additional Material:
2 Tab.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/prac.19793210318
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