Facile synthesis of 6-(heptadec-8-enyl)thiopyrimidines incorporating glycosyl moiety and their antitumor activity

A facile, convenient, and high yielding synthesis of a new series of pyrimidine N- and S-glycosides incorporating an oleyl residue from readily available starting materials was developed. The key step of this protocol is the formation of a 2-thioxopyrimidine as aglycon which is coupled with an activated cyclic and acyclic halo sugar in the presence of sodium hydride. In addition, 5-fluorouracil analogues containing an oleyl moiety were prepared. The in vitro anticancer activity of the newly synthesized compounds was evaluated against two human cancer cell lines, namely MCF-7 (breast) and HEPG2 (liver) carcinoma. The compounds exhibited moderate to high activities with IC 50 values of 13.2–34.2 μM for MCF-7 and 16.2–63.8 μM for HEPG-2 cell lines. 5-Fluorouracil derivatives incorporating a fatty residue are therefore potent against both cell lines. Graphical abstract