Syntheses of antifungal isocoumarins. III. Synthesis and antifungal activity of 3-aryl-3,4-dihydro-4-substituted-isocoumarins.

Abstract
Various cis- and trans-3-aryl-3,4-dihydro-8-(hydroxy or methoxy)isocoumarin-4-carboxylic acids and their methyl esters were prepared. In addition, cis- and trans-3,4-dihydro-8-(hydroxy or methoxy)-4-hydroxyacetyl-3-phenylisocoumarins, cis- and trans-4-diazoacetyl-3,4-dihydro-8-methoxy-3-phenylisocoumarins, trans-4-acetoxyacetyl-3,4-dihydro-8-methoxy-3-phenylisocoumarin and trans-4-acetyl-3,4-dihydro-8-(hydroxy or methoxy)-3-phenylisocoumarins were prepared. All the 3,4-dihydroisocoumarins thus prepared were examined in vitro for antifungal activity. The introduction of a carboxyl, carbomethoxy, acetyl, diazoacetyl or hydroxyacetyl group at the 4-position of the 3,4-dihydroisocoumarin nucleus resulted in the disappearance of the activity.

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