Adam Mieczkowski, Małgorzata A. Makowska, Justyna Sekuła
Nov 4, 2015
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Influential Citations
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Quality indicators
Journal
Tetrahedron
Abstract
Abstract A series of sixteen hitherto unknown Cytarabine analogues bearing a bicyclic 3 H -pyrrolo[2,3- d ]pyrimidin-2(7 H )-one base modified with aryl, pyridyl, benzyl and alkyl substituents was prepared in a straightforward approach. This is the one of the few examples of the synthesis of pyrrolo[2,3- d ]pyrimidin-2(7 H )-one nucleosides and the first example of pyrrolo[2,3- d ]pyrimidin-2(7 H )-one nucleosides possessing arabinose moiety. For the first time, the conversion of the furopyrimidine arabinoside products to a series of novel pyrrolopyrimidines by ammonolysis reaction was thoroughly investigated using aqueous and methanolic reaction conditions under classical and micro-wave heating. This approach resulted in a small library of compounds, which were evaluated for their antiproliferative properties against HL-60 and Jurkat E6.1 cell lines. All synthesized compounds exhibited a weaker cytotoxic effect in comparison to the mother compound. Of all the tested compounds, the derivative bearing a 4- n -pentylphenyl substituent exhibited the highest antiproliferative activity.