Synthesis of New Curcumin-like Pentadienones by O- and C-glycosylation-Reference-Cited by-同舟云学术

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

Published:2019-11-26 Issue:18 Volume:23 Page:1984-1991
ISSN:1385-2728
Container-title:Current Organic Chemistry
language:en
Short-container-title:COC

Author:

Gonçalves Carolina P.¹^ORCID,Michalik Dirk²,Almeida Manuel³,Ribeiro Anderson O.¹,Quincoces José A.⁴

Affiliation:

1. Center for Natural and Human Sciences, Federal University of ABC, Avenida do Estado 5001, 09210-580 Santo Andre, Brazil

2. Institut für Chemie, Universität Rostock, Albert-Einstein-Straße 3a, 18059 Rostock, Germany

3. Mackenzie Presbiterian University. Rua da Consolacao, 896, 01302-907, Sao Paulo, Brazil

4. Laboratory of Organic Synthesis, Anhanguera University of Sao Paulo, Avenida Raimundo Pereira de Magalhaes 3305, 05145-200 São Paulo, Brazil

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.

Funder

Coordination for the Improvement of Higher Education Personnel

Publisher

Bentham Science Publishers Ltd.

Subject

Organic Chemistry

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