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Pregled bibliografske jedinice broj: 43944

Synthesis and biological activities of novel pyrimidine derivatives of 4,5-didehydro-5,6-dideoxy-L-ascorbic acid


Raić-Malić, Silvana; Slade, Neda; Svedružić, Draženka; Gazivoda, Tatjana; Nagl, Ante; Hergold-Brundić, Antonija; Balzarini, Jan; De Clercq, Erik; Spaventi, Radan; Pavelić, Krešimir; Mintas, Mladen
Synthesis and biological activities of novel pyrimidine derivatives of 4,5-didehydro-5,6-dideoxy-L-ascorbic acid // 2nd International Conference on Signal transduction
Dubrovnik, Hrvatska, 2000. str. 111-111 (poster, međunarodna recenzija, sažetak, znanstveni)


Naslov
Synthesis and biological activities of novel pyrimidine derivatives of 4,5-didehydro-5,6-dideoxy-L-ascorbic acid

Autori
Raić-Malić, Silvana ; Slade, Neda ; Svedružić, Draženka ; Gazivoda, Tatjana ; Nagl, Ante ; Hergold-Brundić, Antonija ; Balzarini, Jan ; De Clercq, Erik ; Spaventi, Radan ; Pavelić, Krešimir ; Mintas, Mladen

Vrsta, podvrsta i kategorija rada
Sažeci sa skupova, sažetak, znanstveni

Izvornik
2nd International Conference on Signal transduction / - , 2000, 111-111

Skup
2nd International Conference on Signal transduction

Mjesto i datum
Dubrovnik, Hrvatska, 26-31.05.2000

Vrsta sudjelovanja
Poster

Vrsta recenzije
Međunarodna recenzija

Ključne riječi
Pyrimidine derivatives of 2;3-O;O-dibenzyl-6-deoxy-L-ascorbic acid and 4;5-didehydro-5;6-dideoxy-L-ascorbic acid; synthesis; antitumor activities

Sažetak
The new pyrimidine derivatives of 2,3-O,O-dibenzyl-6-deoxy-L-ascorbic acid (8-10) were synthesised by condensation of uracil and its 5-fluoro and 5-trifluoromethyl substituted derivatives with 4-(5,6-epoxypropyl)-2,3-O,O-dibenzyl-L-ascorbic acid (7), while pyrimidine derivatives of 4,5-didehydro-5,6-dideoxy-L-ascorbic acid (14-17) with free C-2' and C-3' hydroxy groups in the lactone ring were obtained by debenzylation of 11-13 with boron trichloride. Z-Configuration of the C-(4')=C(5') double bond and position of the benzyl group in the lactone ring of 14 were deduced from their 1H and 13C NMR spectra and connectivities in COSY, ROESY and HMBC spectra. The exact stereostructure of 13 was confirmed by its X-ray crystal structure analysis. Of all compounds in the series, the compound 16 containing 5-fluoro-substituted uracil ring showed the most significant antitumor activities against murine leukemia L1210/0 (IC_50 = 1.4 microg/mL), murine mammary carcinoma FM3A/0 (IC_50 = 0.78 microg/mL) and, to a lesser extent, human T-lymphocyte cells Molt4/C8 (IC_50= 31.8 microg/mL) and CEM/0 cell lines (IC-_50 = 20.9 microg/mL).

Izvorni jezik
Engleski

Znanstvena područja
Kemija