Synthesis and cytotoxic activity of novel 5-substituted-1-(β-L-arabinofuranosyl) pyrimidine nucleosides.
A series of new 5-halogeno-1-(ß-L-arabinofuranosyl)uracils and their cytosine analogues were synthesized by halogenation of ara-L-uridine and ara-L-cytidine, respectively. The 5-(2-thienyl) and 5-halogenothienyl derivatives of both series were also prepared in excellent yields by Stille coupling followed by halogenation. All of these syntheses were based on benzoyl-protected derivatives. In vitro cytotoxicity experiments carried out using L1210 mouse leukemia cells showed that 5-(2-thienyl)-ara-L-uridine was the most potent compound of the new compounds; the majority of the analogues were not effective up to 200 μM concentrations.
Institute of Organic Chemistry, Research Center of Natural Sciences, Hungarian Academy of Sciences, Budapest, Hungary.
Róbert
R
Sendula
Erika
E
Orbán
Ferenc
F
Hudecz
Gyula
G
Sági
István
I
Jablonkai
D000818:Animals; D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D045744:Cell Line, Tumor; D060326:Chemistry Techniques, Synthetic; D003596:Cytosine / Q000737:chemistry; D054879:Halogenation; D020128:Inhibitory Concentration 50; D051379:Mice; D011741:Pyrimidine Nucleosides / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D014498:Uracil / Q000737:chemistry
D000970:Antineoplastic Agents; D011741:Pyrimidine Nucleosides; D014498:Uracil; D003596:Cytosine