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Current Organic Chemistry

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ISSN (Print): 1385-2728
ISSN (Online): 1875-5348

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Research Article

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

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

Volume 23, Issue 18, 2019

Page: [1984 - 1991] Pages: 8

DOI: 10.2174/1385272823666191014165754

Price: $65

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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