Syntheses and bioactivities of 1-(hydroxyphenyl)-1-nonen-3-ones and related ethers and esters

A number of nuclear hydroxy styryl ketones and related compounds were prepared and evaluated for antineoplastic and antimicrobial activities as well as for analgesic, anti-inflammatory, and antianaphylactic properties. The second-order rate constants for the reaction of several esters with hydroxide ion in aqueous dioxane (50% v/v) at 36.9 degrees were determined. The screening results showed that activity against P-388 lymphocytic leukemia was found solely with the ethers and that antimicrobial properties were obtained virtually exclusively with the phenolic derivatives. All compounds showed analgesic properties, except for four that were algesic. While little anti-inflammatory activity was found, several compounds showed some antianaphylaxis.