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Morita-Baylis-Hillman modifications on hydroformylated (R)-limonene
José Ribeiro Gregório1, Ricardo Gomes da Rosa1, Bruno Mascarenhas Oliveira1
1Departamento de Química Inorgânica, Universidade Federal do Rio Grande do Sul, Porto Alegre, Rio Grande do Sul, Brazil.
None:
We report the sequential hydroformylation of (R)-limonene followed by Morita-Baylis-Hillman (MBH) coupling to give two new MBH adducts derived from methyl acrylate (adduct 1, 32% isolated yield) and acrylonitrile (adduct 2, 95% isolated yield). The compounds were characterized by 1H- and 13C-NMR, IR spectroscopy and elemental analysis. Biological screening against protozoa, bacteria, fungi and human cell lines revealed modest antiprotozoal and antimicrobial activity, and the ester adduct (adduct 1) showed the most promising antiproliferative activity (CC50 values: HT-29 = 211.4 ± 49.1 μg ml-1; PC-3 = 48.0 ± 2.6 μg ml-1; HeLa = 37.9 ± 6.7 μg ml-1; HACAT = 53.3 ± 3.1 μg ml-1). These results introduce a new set of terpene-derived MBH adducts with preliminary antitumoural potential and encourage further optimization and mechanistic studies.
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