Benzisoxazolones: antimicrobial and antileukemic activity

An unusual acid-mediated rearrangement of o-nitrostyrene oxide afforded 1-(hydroxymethyl)-2,1-benzisoxazol-3(1H)-one which exhibited broad-spectrum antimicrobial and cytotoxic activity. A number of analogues were prepared by employing a modified zinc-reduction procedure on o-nitrobenzoate. Several of these analogues exhibited interesting antipseudomonal activity in agar and broth but were ineffective in vivo.