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The novel pyrimidine and purine derivatives of L-ascorbic acid: synthesis, one- and two-dimensional 1H and 13C NMR study, cytostatic and antiviral evaluation (CROSBI ID 106801)

Prilog u časopisu | izvorni znanstveni rad | međunarodna recenzija

Gazivoda, Tatjana ; Plevnik, Miha ; Plavec, Janez ; Kraljević, Sandra ; Kralj, Marijeta ; Pavelić, Krešimir ; Balzarini, Jan ; De Clercq, Erik ; Mintas, Mladen ; Raić-Malić, Silvana The novel pyrimidine and purine derivatives of L-ascorbic acid: synthesis, one- and two-dimensional 1H and 13C NMR study, cytostatic and antiviral evaluation // Bioorganic & medicinal chemistry, 13 (2005), 1; 131-139. doi: 10.1016/j.bmc.2004.09.052

Podaci o odgovornosti

Gazivoda, Tatjana ; Plevnik, Miha ; Plavec, Janez ; Kraljević, Sandra ; Kralj, Marijeta ; Pavelić, Krešimir ; Balzarini, Jan ; De Clercq, Erik ; Mintas, Mladen ; Raić-Malić, Silvana

engleski

The novel pyrimidine and purine derivatives of L-ascorbic acid: synthesis, one- and two-dimensional 1H and 13C NMR study, cytostatic and antiviral evaluation

The syntheses of the novel C-5 substituted pyrimidine derivatives of L-ascorbic acid containing free hydroxy groups at C-2' (6-10) or C-2' and C-3' (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-2' (18) and C-2' and C-3' (19 and 20). Z- and E-configuration of the C4' =C5' double bond 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 against all human malignant cell lines (IC50: 5.6 - 12.8 uM) except on human T-lymphocytes. Besides, this compound influenced the cell cycle by increasing the cell population in G2/M 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 (IC50: 6.8 uM) and MiaPaCa-2 cells (IC50: 6.5 uM). The compound 20 with 6-(N-pyrrolyl)purine moiety showed the best differential inhibitory effect against MCF-7 cells (IC50: 35.9 uM).

pyrimidine and purine derivatives of L-ascorbic acid ; E- and Z-isomers ; cytostatic activity ; antiviral activity ; apoptosis

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Podaci o izdanju

13 (1)

2005.

131-139

objavljeno

0968-0896

1464-3391

10.1016/j.bmc.2004.09.052

Povezanost rada

Kemija, Temeljne medicinske znanosti

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