Synthesis and antialgal activity of dihydrophenanthrenes and phenanthrenes II: mimics of naturally occurring compounds in Juncus effusus.
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.
Dellagreca
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Dipartimento di Chimica Organica e Biologica, Università Federico II, Via Mezzocannone 16, 1-80134 Naples, Italy.
Fiorentino
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Monaco
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Pinto
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Previtera
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Zarrelli
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D000460:Chlorophyta / Q000187:drug effects* / Q000254:growth & development; D019684:Magnoliopsida / Q000737:chemistry*; D018716:Molecular Mimicry; D010616:Phenanthrenes / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D013329:Structure-Activity Relationship
D010616:Phenanthrenes