Structure-activity relationships of hybrid annonaceous acetogenins: Powerful growth inhibitory effects of their connecting groups between heterocycle and hydrophobic carbon chain bearing THF ring on human cancer cell lines

Naoto Kojima, Tetsuya Fushimi, Takahiro Tatsukawa, Takehiko Yoshimitsu, Tetsuaki Tanaka, Takao Yamori, Shingo Dan, Hiroki Iwasaki, Masayuki Yamashita

Research output: Contribution to journalArticle

16 Citations (Scopus)

Abstract

Five novel hybrid molecules of annonaceous acetogenins and insecticides targeting mitochondrial complex I were synthesized and their growth inhibitory activities against 39 human cancer cell lines were investigated. It was revealed that the connecting group between the N-methylpyrazole part and the hydrophobic alkyl chain bearing the THF ring influenced their biological activities significantly. Amide-connected analog 2, in particular, showed selective and very potent activity (<10 nM) against some cancer cell lines.

Original languageEnglish
Pages (from-to)833-839
Number of pages7
JournalEuropean Journal of Medicinal Chemistry
Volume63
DOIs
Publication statusPublished - Apr 16 2013
Externally publishedYes

Keywords

  • Annonaceous acetogenin
  • Antitumor agent
  • Chemical synthesis
  • Structure-activity relationship

ASJC Scopus subject areas

  • Pharmacology
  • Drug Discovery
  • Organic Chemistry

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