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Synthesis of Prenylated Benzaldehydes and Their Use in the Synthesis of Analogues of Licochalcone A.

✍ Scribed by Hasse Kromann; Mogens Larsen; Thomas Boesen; Kristian Shoenning; Simon Feldbaek Nielsen

Publisher
John Wiley and Sons
Year
2005
Weight
26 KB
Volume
36
Category
Article
ISSN
0931-7597

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✦ Synopsis

Other bioactive products U 1300

Synthesis of Prenylated Benzaldehydes and Their Use in the Synthesis of Analogues of Licochalcone A. -Analogues of licochalcone A, which are used for the exploration of the pharmacophoric elements that are essential for the antibacterial activity, are prepared by using a generally applicable synthesis of prenylated aromatic compounds, as exemplified by prenylated benzaldehydes such as (XI). The hydroxy group in the A-ring is essential for activity whereas the hydroxy group in the B-ring has no influence on the antibacterial effect of licochalcone A. Moreover, the prenyl group of the B-ring can be replaced by other lipophilic long-chained aliphatic substituents, cf.

(XIV). The Claisen-Schmidt condensation of acetophenone (XII) with (XI) provides the best results when the hydroxyacetophenone is protected as the tetrahydropyranyl ether (XII), yielding chalcone (XIII).

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