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2005
Other bioactive products
U 1300
Synthesis of Prenylated Benzaldehydes and Their Use in the Synthesis of Analoof Licochalcone A. — Analogues of licochalcone A, which are used for the
11- 243 gues
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). — (KROMANN, H.; LARSEN, M.; BOESEN,
T.; SHOENNING, K.; NIELSEN*, S. F.; Eur. J. Med. Chem. 39 (2004) 11, 993-1000;
Lica Pharm. A/S, DK-2100 Copenhagen, Den.; Eng.) — H. Hoennerscheid
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