| Name: | Description: | Size: | Format: | |
|---|---|---|---|---|
| 2.22 MB | Adobe PDF |
Advisor(s)
Abstract(s)
Chromones are a group of naturally occurring compounds with a benzoannelated ypyrone
ring. A large number of chromone derivatives have been isolated from natural
sources and a wide range of biological properties have been attribute to them, such as antifungal,
anti-allergenic, antiviral, antitubulin, anti-hypertensive, anticancer and antioxidant
activities.1 11 Studies with 2-styrylchromones demonstrated that the number and position of
the hydroxyl groups in the A-ring and the 3', 4'-dihydroxy substitution on B-ring play an
important role in their radical scavenger activity. In addition the molecular stabilization
promoted by the carbonyl carbon C-4 and Ca=C~ double bond, also seem to contribute to
the scavenging effect of these compounds. 121
Taking into account these considerations we establi sh a new synthetic route for the
preparation of novel hydroxylated 2-butadienylchromone derivatives 5. Our methodology
involves the condensation of methoxy-2-methylchromones zl31 with 3,4-dimethoxy-
cinnamaldehyde 3141 leading to (E,E)-2-( 4-arylbuta-1 ,3-dien-l-yl)-4H-chromen-4-ones 4.
The final step involves the cleavage of methyl group of 4 in order to obtain the desired
hydroxylated derivatives 5 (Scheme). In this communication we will present the synthetic
details of all described transformations as well as the structural characterisation (by ID and
2D NMR studies) of the new synthesi sed compounds.
Description
Keywords
Citation
Albuquerque, Hélio; Santos, Clementina M. M.; Esteves, Cátia; Silva, Artur; Cavaleiro, José (2012). Synthesis of novel 2-Butadienylchromone derivatives. In 3º Encontro Nacional de Química Terapêutica. Aveiro