Antiproliferating Polyquinanes. V. Di- and Triquinanes Involving α-Methylene or α-Alkylidene Cyclopentanone, Cyclopentenone, and γ-Lactone Systems(Organic,Chemical)

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New analogues related to quadrone (3), 3-methyIenetricyclo[4.3.2.0^<1.5>]undecan-4-one (14), 4-methylenetricyclo[4.3.2.0^<1.5>]undecan-3-one (15), and 2-methylenetricyclo[4.3.2.0^<1.5>]undec-4-en-3-one (16), and novel propellane- and angular-type triquinanes, 3-methylenetricyclo[3.3.3.0]undecan-2-one (17), (E)-3-propylidene- and (E)-3-(5-carbomethoxy)pentylidenetricyclo[3.3.3.0]undecan-2-ones (18 and 19), (E)-5-(2-oxotricyclo[3.3.3.0]undecan-3-ylidene)pentyl (E)-cinnamate (20), 2-methylenetricyclo[3.3.3.0]undecan-3-one (21), 4-methylene-2-oxatricyclo[3.3.3.0]undecan-3-one (22), and 7-methylenetricyclo[6.3.0.0^<1.5>]undecan-6-one (23), were readily synthesized through skeletal transformations, and showed antiproliferating activity. Biomimetic reactions of a model compound of 3, 2-methylenetricyclo[4.3.2.0^<1.5>]undecan-3-one (8), with propanethiol, etc, were undertaken. Correlations of the activity of some polyquinanes with second-order rate constants of addition of L-cysteine and with the carbon-13 nuclear magnetic resonance chemical shifts of exomethylene β-carbons are discussed.
社団法人日本薬学会の論文
1987-02-25