Pregled bibliografske jedinice broj: 86046
Synthesis And Biological Evaluation Of Novel Pyrimidine Derivatives Of L-Ascorbic Acid
Synthesis And Biological Evaluation Of Novel Pyrimidine Derivatives Of L-Ascorbic Acid // XV International Round Table "Nucleosides, Nucleotides & Nucleic Acids" / De Clercq, Erik, Herdewijn, Piet (ur.).
Leuven, 2002. str. P-80 (poster, međunarodna recenzija, sažetak, znanstveni)
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Naslov
Synthesis And Biological Evaluation Of Novel Pyrimidine Derivatives Of L-Ascorbic Acid
Autori
Gazivoda, Tatjana ; Prekupec, Svjetlana ; Balzarini, Jan ; De Clercq, Erik ; Mintas, Mladen and Raic-Malic, Silvana
Vrsta, podvrsta i kategorija rada
Sažeci sa skupova, sažetak, znanstveni
Izvornik
XV International Round Table "Nucleosides, Nucleotides & Nucleic Acids"
/ De Clercq, Erik, Herdewijn, Piet - Leuven, 2002, P-80
Skup
XV International Round Table "Nucleosides, Nucleotides & Nucleic Acids"
Mjesto i datum
Leuven, Belgija, 10.09.2002. - 14.09.2002
Vrsta sudjelovanja
Poster
Vrsta recenzije
Međunarodna recenzija
Sažetak
Pyrimidine derivatives of 2,3-O,O-dibenzyl-4,5-didehydro-5,6-dideoxy-L-ascorbic acid (A) and 2,3-O,O-dibenzyl-6-deoxy-L-ascorbic acid (B) were synthesized by condensation of uracil and its 5-substituted derivatives with 5,6-O,O-diacetyl-2,3-O,O-dibenzyl-L-ascorbic acid and 4-(5,6-epoxypropyl)-2,3-O,O-dibenzyl-L-ascorbic acid, respectively. Debenzylation of 2,3-O,O-dibenzyl derivatives of L-ascorbic acid with boron trichloride gave mono- and/or dihydroxy derivatives (A). Z-Configuration of the C(4')=C(5') double bond and position of the benzyl group in the lactone ring of monobenzylated derivatives were deduced from their 1H and 13C NMR spectra and connectivities in COSY, ROESY and HMBC spectra. Of all compounds in the series 5-fluoro-2,3-O,O-dibenzyl-4,5-didehydro-5,6-dideoxy-L-ascorbic acid showed the most significant antitumor activities against leukemia L1210/0 (IC50=1.4 g/mL), murine mammary carcinoma FM3A/0 (IC50=0.78 g/mL) and in a less extent, human T-lymphocyte cells Molt4/C8 (IC50=31.8 g/mL) and CEM/0 cell lines (IC50=20.9 g/mL). This compound was also the most selective in the citostatic activity. It inhibits selectively the L1210/0 and FM3A/0 tumor cells but not the other ones.1, 2 1 S. Raic-Malic, A. Hergold-Brundic, A. Nagl, M. Grdisa, K. Pavelic, E. De Clercq and M. Mintas, J. Med. Chem. (1999), 42, 2673-2678. 2 S. Raic-Malic, D. Svedruzic, T. Gazivoda, A. Hergold-Brundic, A. Nagl, J. Balzarini, E. De Clercq and M. Mintas, J. Med. Chem. (2000), 43, 4806-4811.
Izvorni jezik
Engleski
Znanstvena područja
Kemija
