Concise synthesis of carbazole-1,4-quinones and evaluation of their antiproliferative activity against HCT-116 and HL-60 cells

Takashi Nishiyama, Noriyuki Hatae, Teruki Yoshimura, Sawa Takaki, Takumi Abe, Minoru Ishikura, Satoshi Hibino, Tominari Choshi

Research output: Contribution to journalArticlepeer-review

14 Citations (Scopus)

Abstract

We report a convenient synthesis of carbazole-1,4-quinone alkaloid koeniginequinones A and B using a tandem ring-closing metathesis with the dehydrogenation reaction sequence under an O2 atmosphere as an important step. Using this method, carbazole-1,4-quinones substituted at the 5-, 6-, 7-, and/or 8-positions have been synthesized. Moreover, 24 compounds, including koeniginequinones A and B, have been evaluated for their antiproliferative activity against HCT-116 and HL-60 cells, and the 6-nitro analog exhibited the most potent activity against both tumor cell types.

Original languageEnglish
Pages (from-to)561-577
Number of pages17
JournalEuropean Journal of Medicinal Chemistry
Volume121
DOIs
Publication statusPublished - Oct 4 2016
Externally publishedYes

Keywords

  • Antiproliferative activity
  • Carbazole-1,4-quinone
  • Koeniginequinone A
  • Koeniginequinone B

ASJC Scopus subject areas

  • Pharmacology
  • Drug Discovery
  • Organic Chemistry

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