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Synthesis and antialgal activity of dihydrophenanthrenes and phenanthrenes II: mimics of naturally occurring compounds in Juncus effusus. 2001
Dipartimento di Chimica Organica e Biologica, Università Federico II, Via Mezzocannone 16, 1-80134 Naples, Italy.
9,10-Dihydrophenanthrenes and phenanthrenes, mimics of natural compounds with strong antialgal activity, have been synthesized through cross-coupling by zerovalent Ni of 1-(2-iodo-5-methoxy)-phenylethanol or 2-iodo-5-methoxyacetophenone with iodoxylenes. The synthetic compounds had a hydroxyl or a methoxyl group at C-2 and two methyls in the C ring. Assays on the green alga Selenastrum capricornutum showed that all the compounds, except 2-methoxy-5,7-dimethylphenanthrene, caused strong inhibition of algal growth at 10(-4) M. 2-Hydroxy-7,8-dimethyl-9,10-dihydrophenanthrene and 2-methoxy-5,6-dimethylphenanthrene fully inhibited growth at 10(-5) M.
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