Synthesis and antiproliferative activity of new cyclodiprenyl phenols against select cancer cell lines

Bastián Said, Iván Montenegro, Manuel Valenzuela, Yusser Olguín, Nelson Caro, Enrique Werner, Patricio Godoy, Joan Villena, Alejandro Madrid

Research output: Contribution to journalArticlepeer-review

7 Citations (Scopus)


Six new cyclodiprenyl phenols were synthesized by direct coupling of perillyl alcohol and the appropriate phenol. Their structures were established by IR, HRMS and mainly NMR. Three human cancer cell lines-breast (MCF-7), prostate (PC-3) and colon (HT-29)-were used in antiproliferative assays, with daunorubicin and dunnione as positive controls. Results described in the article suggest that dihydroxylated compounds 2-4 and monohydroxylated compound 5 display selectivity against cancer cell lines, cytotoxicity, apoptosis induction, and mitochondrial membrane impairment capacity. Compound 2 was identified as the most effective of the series by displaying against all cancer cell lines a cytotoxicity close to dunnione antineoplastic agent, suggesting that the cyclodiprenyl phenols from perillyl alcohol deserve more extensive investigation of their potential medicinal applications.

Original languageEnglish
Article number2323
Issue number9
Publication statusPublished - 12 Sept 2018


  • Antiproliferative agents
  • Cyclodiprenyl phenols
  • Perillyl alcohol
  • Synthesis

ASJC Scopus subject areas

  • Analytical Chemistry
  • Chemistry (miscellaneous)
  • Molecular Medicine
  • Pharmaceutical Science
  • Drug Discovery
  • Physical and Theoretical Chemistry
  • Organic Chemistry


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