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The unsaturated acyclic nucleoside analogues bearing a sterically constrained (Z)-4'-benzamido-2'-butenyl moiety : Synthesis, X-ray crystal structure study, cytostatic and antiviral activity evaluations (CROSBI ID 150154)

Prilog u časopisu | izvorni znanstveni rad | međunarodna recenzija

Benci, Krešimir ; Wittine, Karlo ; Radan, Malajka ; Cetina, Mario ; Sedić, Mirela ; Kraljević Pavelić, Sandra ; Pavelić, Krešimir ; deClercq, Erik ; Mintas, Mladen The unsaturated acyclic nucleoside analogues bearing a sterically constrained (Z)-4'-benzamido-2'-butenyl moiety : Synthesis, X-ray crystal structure study, cytostatic and antiviral activity evaluations // Bioorganic & medicinal chemistry, 18 (2010), 17; 6249-6257. doi: 10.1016/j.bmc.2010.07.035

Podaci o odgovornosti

Benci, Krešimir ; Wittine, Karlo ; Radan, Malajka ; Cetina, Mario ; Sedić, Mirela ; Kraljević Pavelić, Sandra ; Pavelić, Krešimir ; deClercq, Erik ; Mintas, Mladen

engleski

The unsaturated acyclic nucleoside analogues bearing a sterically constrained (Z)-4'-benzamido-2'-butenyl moiety : Synthesis, X-ray crystal structure study, cytostatic and antiviral activity evaluations

A series of the novel acyclic unsaturated pyrimidine (1–12) and adenine (13) nucleoside analogues bearing conformationally restricted (Z)-2'-butenyl moiety were synthesized to evaluate their antiviral and cytostatic activity potency against malignant tumor cell lines and normal human fibroblast (WI38). The N-1 and/or N-3 acyclic side chain substitution in pyrimidine ring in N-3 substituted 5-trifluoromethyluracyl derivative (11), N-1, N-3 disubstituted 5-fluorouracyl derivative (12) and adenine derivative (13) was deduced from their 1H and 13C NMR spectra and confirmed by single crystal X-ray structure analysis. The X-ray crystal structure analysis 11-13 revealed also supramolecular self-assemblies that built infinite chains into two- and three–dimensional networks. The results of the in vitro cytostatic activity evaluations of 1-13 indicate that majority of the tested compounds exhibited a non-specific and moderate antiproliferative effect at the highest concentration (100 μM). Of all evaluated compounds on the tested cell lines only N-1-4'' fluoro-substituted-benzamide uracyl derivative (7) showed rather marked and selective inhibitory activity against the growth of MCF-7 cells at concentration of 2.7 µM and no cytotoxic effect on normal fibroblasts WI38. This compound can be therefore considered as potential lead compound for further synthetic structure modification.

unsaturated acyclic nucleoside analogues ; X-ray diffraction ; supramolecular self-assembling ; cytostatic activity ; antiviral activity

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Podaci o izdanju

18 (17)

2010.

6249-6257

objavljeno

0968-0896

10.1016/j.bmc.2010.07.035

Povezanost rada

Kemija, Temeljne medicinske znanosti

Poveznice
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