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Βιοδραστικοί ακόρεστοι κετονουκλεοζίτες: σύνθεση και βιολογική αποτίμηση φθορο-κετονουκλεοζιτών της αδενίνης και της κυτοσίνης

By Στυλιανή Μαντά

Abstract

The aim of the present thesis was the synthesis and the biological evaluation of new series of fluorinated nucleoside analogues with six-membered carbohydrate moieties of N4-benzoylcytosine and N6-benzoyladenine. Based on the interesting biological properties of unsaturated ketonucleosides and deoxy-pyranonucleosides and considering that the introduction of fluorine into the sugar moiety of a nucleoside increases its biological activity, in the present work, the synthesis of new series of fluorinated keto unsaturated and deoxyketo-pyranonucleoside analogues of N4-benzoylcytosine and N6-benzoyladenine respectively, was described. Initially, the synthesis of a new class of nucleoside analogues possessing a fluoro group in the 3΄-position, a keto group in the 4΄- or 2΄-position and deoxy in the 2΄- or 4΄-position of the sugar moiety respectively, was studied. Then, the synthesis of a new class of fluorinated unsaturated ketonucleosides possessing a fluoro group in the 3΄-position, a keto group in the 2΄- or 4΄-position and a double bond in the 3΄,4΄- or 2΄,3΄-positions of the sugar moiety respectively, was described. Finally, a new class of fluorinated deoxy keto unsaturated nucleosides, possessing a fluoro group in the 3΄-position, deoxy in the 6΄-position, a keto group in the 4΄- or 2΄-position and a double bond in the 2΄,3΄- or 3΄,4΄-positions of the sugar moiety respectively, was synthesized. The above nucleoside analogues contained N4-benzoylcytosine or N6-benzoyladenine respectively, as heterocyclic bases. In the present thesis, the biological studies of the newly synthesized compounds were also accomplished, concerning their antiviral, anticancer and antioxidant activity.

Topics: Νουκλεοζίτες, Πυρανονουκλεοζίτες, Κετο-πυρανονουκλεοζίτες, Ακόρεστοι κετονουκλεοζίτες, Δεοξυ-πυρανονουκλεοζίτες, Φθοριωμένοι νουκλεοζίτες
Publisher: University of Thessaly (UTH)
Year: 2008
DOI identifier: 10.12681/eadd/17312
OAI identifier:
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