Synthesis and evaluation of 1-(hydroxyphenyl)-1-nonen-3-ones and related compounds for antineoplastic and antimicrobial activities.

Some 1-(hydroxyphenyl)-1-nonen-3-ones, the corresponding Mannich bases, and O-benzoyl esters were synthesized. Evaluation of these derivatives against murine P-388 lymphocytic leukemia indicated that, while the hydroxyphenyl styryl ketones and related esters were devoid of significant anticancer activities, etherification of the nuclear hydroxyl group gave compounds with a discernible increase in mean survival time. The hydroxyphenyl styryl ketones showed marked potencies against two pathogenic fungi and one, yeast, while the corresponding ethers had diminished activities and the related esters were virtually devoid of antimicrobial activities. Two Mannich bases showed similar spectra of antimicrobial activities as the phenols and, in particular, were active against Trichophyton mentagrophytes and Saccharomyces uvarum.