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  • Title: Synthesis and antitumor activity of tropolone derivatives. 4.
    Author: Yamato M, Hashigaki K, Sakai J, Kawasaki Y, Tsukagoshi S, Tashiro T.
    Journal: J Med Chem; 1987 Jan; 30(1):117-20. PubMed ID: 3806588.
    Abstract:
    Modifications of monotropolone 2 having poor potency against P388 in mice were studied. The alpha-ethoxy group of 2, prepared from hinokitiol and benzaldehyde diethyl acetal, was replaced with a phenolic or heteroaromatic compound by heating 2 with the appropriate nucleophile. Structure-activity relationships indicated that an acidic hydroxyl and a proton-accepting group situated in the neighboring position, which permits the formation of a chelate with a metal ion, contributed to enhanced activity. Among the compounds studied, the 8-hydroxyquinoline analogue 10f was the most favorable compound.
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