The flavanolignan silybin and its hemisynthetic derivatives, a novel series of potential modulators of p-glycoprotein
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2014, TetrahedronCitation Excerpt :The direct prenylation of electron-rich phenolic compounds has been reported, although it is known to be a challenge to obtain selective prenylation at only one position in a compound like 2. The use of prenyl halides in the presence of a base, e.g. DBU,14 tetramethylammonium hydroxide,15,16 potassium hydroxide17,18 or sodium hydride,19,20 failed as C-prenylated products were obtained together with O-prenylated as well as degradation products of 3 (2 is not stable in basic conditions). Next, Lewis acid catalysed condensation of 2-methyl-3-buten-2-ol was attempted.
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2014, European Journal of Medicinal ChemistryCitation Excerpt :A close scrutiny of natural antimalarial chalcones has revealed that a vast majority of these possess substituted allylated aromatic rings (prenyl or geranyl group) as important elements of their pharmacophores. The importance of prenyl or allyl group for enhancing the bioactivities of flavonoids and chalcones is well documented in literature [22,30–33]. Furthermore, the prenyl moiety contributes to the lipophilicity of the molecule, an important requirement for antimalarial activity [34].
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