2-O-Glykosylace N-nesubstituovaných 4-hydroxychinolin-2(1H)-onů

Bc. Alena NĚMCOVÁ

Master's thesis

2-O-Glycosylation of N-Unsubstituted 4-Hydroxyquinolin-2(1H)-ones

Abstract:

Tato práce se zabývá stereoselektivní 2-O-glykosylací N-nesubstituovaných 4 hydroxychinolin-2(1H)-onů na odpovídající 3-substituované 2-O-(?-D-glukopyranosyloxy)-4-hydroxychinoliny. Hydroxylová skupina 4 hydroxychinolin-2(1H)-onu byla chráněna acetylací acetanhydridem v pyridinu a 4-acetyloxyderiváty byly podrobeny glykosylačním reakcím s 2,3,4,6-tetra-O-acetyl-?-D-glukopyranosylbromidem v přítomnosti oxidu stříbrného v acetonitrilu. Tyto reakce poskytly 2-O-(2,3,4,6-tetra-O-acetyl-?-D-glukopyranosyloxy)chinolin-4-yl acetáty v uspokojivých výtěžcích. U získaných sloučenin byly provedeny pokusy o jejich deacetylaci účinkem Et3N nebo NH3 v MeOH. Prakticky u všech získaných produktů byla jejich charakterizace provedena běžnými spektrálními metodami (ESI-MS, EI-MS a IČ). U několika studovaných sloučenin bylo změřeno NMR.

Abstract:

This diploma thesis deals with stereoselective 2-O-glucosylation of N-unsubstituted 4-hydroxyquinolin-2(1H)-one into 3-substituted 2-(?-D-glucopyranosyloxy)-4-hydroxyquinolines. Hydroxyl group of quinolinone was protected by acetylation using acetic anhydride in pyridine and the 4-O-acetyl derivatives were treated with 2,3,4,6-tetra-O-acetyl-?-D-glucopyranosyl bromide and silver oxide in acetonitrile. The reaction furnished 2-(2,3,4,6-tetra-O-acetyl-?-D-glu?copyranosyloxy)quinolin-4-yl acetates in satisfactory yields. The gained products were deacetylated with Et3N in MeOH and NH3 in MeOH. Practically all of the gained products were characterized by common spectral methods (ESI-MS, EI-MS and IR spectroscopy). Several of the studied compounds were measured by NMR spectroscopy.

Keywords

4-Hydroxychinolin-2(1H)-ony, Acetobrom-?-D-glukosa, 2-O-Glykosylace, Koenigsova-Knorrova metoda, Deacetylace.

Language used: Czech

Date on which the thesis was submitted / produced: 7. 5. 2012

Accessible from:: 7. 5. 2012

Thesis defence

• Supervisor: Ing. Roman Kimmel, Ph.D.

Tomas Bata University in Zlín

Faculty of Technology

Master programme / field:
Chemistry and Food Technologies / Food Chemistry and Chemistry of Bioactive Substances