Antiproliferating Polyquinanes. V.1) Di- and Triquinanes Involving α-Methylene or α-Alkylidene Cyclopentanone, Cyclopentenone, and γ-Lactone Systems

Kiyomi Kakiuchi*, Masaki Ue, Mitsunori Takeda, Toshihiro Tadaki, Yuji Kato, Teruhisa Nagashima, Yoshito Tobe, Yoshinobu Odaira, Hiroshi Koike, Nobutaka Ida

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

12 Scopus citations

Abstract

New analogues related to quadrone (3), 3-methylenetricyclo[4.3.2.01-5]undecan-4-one (14), 4-methylenetricyclo [4.3.2.01, 5]undecan-3-one (15), and 2-methylenetricyclo[4.3.2.01, 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[6.3.0.01-5]undecan-6-one (23), were readily synthesized through skeletal transformations, and showed antiproliferating activity. Biomimetic reactions of a model compound of 3, 2-methylenetricyclo[4.3.2.01-5]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 exo-methylene β-carbons are discussed.

Original languageEnglish
Pages (from-to)617-631
Number of pages15
JournalChemical and Pharmaceutical Bulletin
Volume35
Issue number2
DOIs
StatePublished - 1 Jan 1987

Keywords

  • 13C-NMR chemical shift
  • antiproliferating activity
  • biomimetic reaction
  • cytotoxic functional group
  • diquinane
  • quadrone
  • second-order rate constant
  • structure-activity relationship
  • triquinane
  • α-methylene cyclopentanone

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