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

[ Vol. 23 , Issue. 18 ]

Author(s):

Carolina P. Gonçalves*, Dirk Michalik*, Manuel Almeida, Anderson O. Ribeiro and José A. Quincoces   Pages 1984 - 1991 ( 8 )

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.

Affiliation:

Center for Natural and Human Sciences, Federal University of ABC, Avenida do Estado 5001, 09210-580 Santo Andre, Institut für Chemie, Universität Rostock, Albert-Einstein-Straße 3a, 18059 Rostock, Mackenzie Presbiterian University. Rua da Consolacao, 896, 01302-907, Sao Paulo, Center for Natural and Human Sciences, Federal University of ABC, Avenida do Estado 5001, 09210-580 Santo Andre, Laboratory of Organic Synthesis, Anhanguera University of Sao Paulo, Avenida Raimundo Pereira de Magalhaes 3305, 05145-200 São Paulo

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