Alvarez S, Pazos-Randulfe Y, Khanwalkar H, Germain P, Alvarez R, Gronemeyer H, de Lera AR
New retinoid chemotypes: 9-cis-Retinoic acid analogs with hydrophobic rings derived from terpenes as selective RAR agonists. [Journal Article]
Bioorg Med Chem 2008 Nov 15; 16(22):9719-28.
A series of 9-cis-retinoic acid analogs modified at the hydrophobic ring with a (bi)cyclohexenyl moiety derived from natural terpenes has been stereoselectively prepared using a Suzuki cross-coupling as key step. Transient transactivation studies indicate that modification of the hydrophobic ring impacts dramatically on RXR-binding and transactivation, with most retinoids being inactive on RXRbeta, while preserving their RAR pan-agonist profile. Furthermore, only the RARgamma subtype was capable of enantiomeric discrimination with some pairs of enantiomeric terpene-retinoids.
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