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The novel C-5 aryl, alkenyl, and alkynyl substituted uracil derivatives of L-ascorbic acid: Synthesis, cytostatic, and antiviral activity evaluations (CROSBI ID 130855)

Prilog u časopisu | izvorni znanstveni rad | međunarodna recenzija

Gazivoda, Tatjana ; Raić-Malić, Silvana ; Marjanović, Marko ; Kralj, Marijeta ; Pavelić, Krešimir ; Balzarini, Jan ; De Clercq, Erik ; Mintas, Mladen The novel C-5 aryl, alkenyl, and alkynyl substituted uracil derivatives of L-ascorbic acid: Synthesis, cytostatic, and antiviral activity evaluations // Bioorganic & medicinal chemistry, 15 (2007), 2; 749-758. doi: 10.1016/j.bmc.2006.10.046

Podaci o odgovornosti

Gazivoda, Tatjana ; Raić-Malić, Silvana ; Marjanović, Marko ; Kralj, Marijeta ; Pavelić, Krešimir ; Balzarini, Jan ; De Clercq, Erik ; Mintas, Mladen

engleski

The novel C-5 aryl, alkenyl, and alkynyl substituted uracil derivatives of L-ascorbic acid: Synthesis, cytostatic, and antiviral activity evaluations

The novel C-5 substituted uracil derivatives of L-ascorbic acid were synthesized by coupling of 5-iodouracil-4, 5-didehydro-5, 6-dideoxy-L-ascorbic acid with unsaturated stannanes under Stille reaction conditions. The new compounds were evaluated for their antitumoral and antiviral activities. Among all compounds evaluated the 5-propynyl substituted uracil derivative of L-ascorbic acid (7) exhibited the most pronounced cytostatic activities against all examined tumor cell lines (IC50: 0.2-0.78 μ M). However, this compound was also cytotoxic to human normal fibroblasts WI 38. The 5-(phenylethynyl)uracil-2, 3-di-O-benzylated L-ascorbic acid derivative (4) exhibited an albeit slight (IC50: 55-108 μ M), but selective inhibitory effect towards all tumor cell lines except for cervical carcinoma (HeLa), pancreatic carcinoma (MiaPaCa-2), laryngeal carcinoma (Hep-2) and colon carcinoma (SW 620), and no cytotoxicity to normal human fibroblast (WI 38). Compound 7 showed some, not highly specific inhibitory potential against vesicular stomatitis virus, Coxackie B4 virus and Sindbis viruses (EC50: 1.6 μ M).

L-ascorbic acid ; C-5 substituted uracil derivatives ; cytostatic activities ; antiviral activities

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Podaci o izdanju

15 (2)

2007.

749-758

objavljeno

0968-0896

1464-3391

10.1016/j.bmc.2006.10.046

Povezanost rada

Kemija, Temeljne medicinske znanosti

Poveznice