New retinoid chemotypes: 9-cis-retinoic acid analogs with hydrophobic rings derived from terpenes as selective RAR agonists. - Archive ouverte HAL Access content directly
Journal Articles Bioorganic and Medicinal Chemistry Year : 2008

New retinoid chemotypes: 9-cis-retinoic acid analogs with hydrophobic rings derived from terpenes as selective RAR agonists.

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Abstract

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.

Dates and versions

inserm-00350716 , version 1 (07-01-2009)

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Susana Alvarez, Yolanda Pazos-Randulfe, Harshal Khanwalkar, Pierre Germain, Rosana Alvarez, et al.. New retinoid chemotypes: 9-cis-retinoic acid analogs with hydrophobic rings derived from terpenes as selective RAR agonists.. Bioorganic and Medicinal Chemistry, 2008, 16 (22), pp.9719-28. ⟨10.1016/j.bmc.2008.09.069⟩. ⟨inserm-00350716⟩
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