1040562-89-7Relevant academic research and scientific papers
Synthesis, cytostatic and anti-HIV evaluations of the new unsaturated acyclic C-5 pyrimidine nucleoside analogues
Gazivoda, Tatjana,Raic-Malic, Silvana,Kristafor, Vedran,Makuc, Damjan,Plavec, Janez,Bratulic, Sinisa,Kraljevic-Pavelic, Sandra,Pavelic, Kresimir,Naesens, Lieve,Andrei, Graciela,Snoeck, Robert,Balzarini, Jan,Mintas, Mladen
, p. 5624 - 5634 (2008)
A series of the novel C-5 alkynyl pyrimidine nucleoside analogues (1-14) in which the sugar moiety was replaced by the conformationally restricted Z- and E-2-butenyl spacer between the phthalimido and pyrimidine ring were synthesized by using Sonogashira cross-coupling reaction. Cytostatic activity evaluation of the novel compounds showed that E-isomers exhibited, in general, better cytostatic activities than the corresponding Z-isomers. E-isomer 14 exhibited the best cytostatic effect against all evaluated malignant cell lines, particularly against hepatocellular carcinoma (Hep G2, IC50 = 4.3 μM). However, this compound was also cytotoxic to human normal fibroblasts (WI 38). Its Z-isomer 7 showed highly specific antiproliferative activity against Hep G2 (IC50 = 18 μM) and no cytotoxicity to WI 38. Moreover, compounds 3, 4 and 14 expressed some marginal inhibitory activity against HIV-1 and HIV-2.
