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The novel pyrimidine and purine derivatives of L-ascorbic acid : synthesis, one- and two-dimensional ▫$^1H$▫ and ▫${13}C$▫ NMR study, cytostatic and antiviral evaluation
Gazivoda, Tatjana ...
The syntheses of the novel C-5 substituted pyrimidine derivatives of L-ascorbic acid containing free hydroxy groups at C-2ć (6-10) or C-2ć and C-3ć(11-15) positions of the lactone ring are described. ...Debenzylation of the 6-chloro- and 6-(N-pyrrolyl)purine derivatives of 2,3-O,O-dibenzyl-L-ascorbic acid (16 and 17) gave the new compounds containing hydroxy groups at C-2ć (18)and C-2ć and C-3ć (19 and 20). Z- and E-configuration of the C4ćC5ć doublebond and position of the lactone ring of the compounds 6-9 were deduced from their one- and two-dimensional 1H and 13C NMR spectra and connectivities in NOESY and HMBC spectra. Compounds 15 and 18 showed the best inhibitory activities of all evaluated compounds in the series. The compound 15 containing 5-(trifluoromethyl)uracil showed marked inhibitory activity againstall human malignant cell lines (IC50Č 5.6-12.8 M) except on human T-lymphocytes. Besides, this compound influenced the cell cycle by increasing the cell population in G2žM phase and induced apoptosis in SW 620 and MiaPaCa-2 cells. The compound 18 containing 6-chloropurine ring expressed the most pronounced inhibitory activities against HeLa (IC50Č 6.8 M) and MiaPaCa-2 cells (IC50Č 6.5 M). The compound 20 with 6-(N-pyrrolyl)purine moiety showed the best differential inhibitory effect against MCF-7 cells (IC50Č 35.9 M).
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