Syntheses of antifungal isocoumarins. II. Synthesis and antifungal activity of 3-substituted isocoumarins.

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Abstract
Various 3-arylisocoumarins (5, 6, 8, 10, 11 and 12) were simply prepared in high yields by heating homophthalic acids (1.sbd.4) with aromatic acyl chlorides. 8-Hydroxy-3-phenylisocoumarin (17) and 8-acetoxy-3-phenylisocoumarin (18), and 8-hydroxy-3-(p-methoxyphenyl)isocoumarin (19) were obtained by alkaline hydrolysis of 10 and 11, respectively, followed by treatment with acetic anhydride. 3,4-Dihydro-8-hydroxy-3-phenylisocoumarin (24) was prepared from 10 by alkaline hydrolysis followed by reduction with sodium borohydride then heating with acetic anhydride. 3-(p-Hydroxyphenyl)-isocoumarin (7), 8-hydroxy-3-(p-hydroxyphenyl)isocoumarin (9), 5-chloro-8-hydroxy-6-methoxy-3-phenylisocoumarin (13) and 3,4-dihydro-3-(p-hydroxyphenyl)isocoumarin (23) were prepared by demethylation of 6, 8, 12 and 22, respectively. All the prepared isocoumarins and some other isocoumarin derivatives (25.sbd.30) were examined in vitro for antifungal activity. The structure-activity relationships are discussed.

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