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Current Organic Chemistry

Author(s): Carolina P. Gonçalves*, Dirk Michalik*, Manuel Almeida, Anderson O. Ribeiro and José A. Quincoces

DOI: 10.2174/1385272823666191014165754

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Synthesis of New Curcumin-like Pentadienones by O- and C-glycosylation

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Abstract

A new method for the preparation of three new curcumin analogues is described by the connection of pentadienones to carbohydrate units. From L-Rhamnose and D-Galactose, several functionalization reactions were performed to obtain the desired sugar units. The sugars 8, 18 and 19, after obtained, were used as starting material for the association with curcumin-derived pentadienones, thus giving rise to three new chalcones 9 by O-glycosylation, 22 and 23 C-glycosylation. The new compounds were characterized by NMR and mass spectroscopy. The compounds obtained have high potential to exhibit antitumor activity.

Keywords: L-Rhamnose derivatives, D-Galactose derivatives, pentadienone, curcumin analogues, O-glycosylation, C-glycosylation.

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