Identification of a chromone-based retinoid containing a polyolefinic side chain via facile synthetic routes |
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Authors: | Weilin Sun Patrick J Carroll Dianne R Soprano Daniel J Canney |
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Institution: | 1. Department of Pharmaceutical Sciences, School of Pharmacy, Temple University, 3307 N. Broad Street, Philadelphia, PA 19140, USA;2. Department of Biochemistry, School of Medicine, Temple University, 3307 N. Broad Street, Philadelphia, PA 19140, USA;3. Department of Chemistry, University of Pennsylvania, 231 S. 34th Street, Philadelphia, PA 19104, USA |
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Abstract: | Attempts to prepare substituted chromones as novel retinoids revealed that some chromones were unstable under Wadsworth–Horner–Emmons reaction conditions. Hence, Wittig reactions were used to prepare chromone-based compounds as potential retinoids. Firstly, Wittig reagents prepared from 3-bromomethyl-chromen-4-one were reacted with olefinic-aldehydes to provide the target compounds with all-trans side chains in good yield. The approach supplies a useful general route to structurally diverse chromone-based compounds possessing a variety of side chains. Sequential Wittig reactions were used also to prepare a chromone-based retinoid. These novel compounds were evaluated in binding assays and a high affinity RAR ligand was identified. Crystal structures obtained for two key precursors aided the interpretation of binding data. |
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