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Pregled bibliografske jedinice broj: 154245

The Novel Pyrimidine and Purine Derivatives of L-ascorbic Acid: Synthesis, One- and Two-Dimensional 1H and 13C NMR Study, Cytostatic and Antiviral Evaluation


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), 131-139 (međunarodna recenzija, članak, znanstveni)


Naslov
The Novel Pyrimidine and Purine Derivatives of L-ascorbic Acid: Synthesis, One- and Two-Dimensional 1H and 13C NMR Study, Cytostatic and Antiviral Evaluation

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

Izvornik
Bioorganic & medicinal chemistry (0968-0896) 13 (2005); 131-139

Vrsta, podvrsta i kategorija rada
Radovi u časopisima, članak, znanstveni

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

Sažetak
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).

Izvorni jezik
Engleski

Znanstvena područja
Kemija, Temeljne medicinske znanosti



POVEZANOST RADA


Projekt / tema
0098092
0098093
0125003

Ustanove
Institut "Ruđer Bošković", Zagreb,
Fakultet kemijskog inženjerstva i tehnologije, Zagreb

Časopis indeksira:


  • Current Contents Connect (CCC)
  • Web of Science Core Collection (WoSCC)
    • Science Citation Index Expanded (SCI-EXP)
    • SCI-EXP, SSCI i/ili A&HCI
  • Scopus
  • MEDLINE


Uključenost u ostale bibliografske baze podataka:


  • Chemical Abstracts