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

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

  • Eur J Med Chem. 2016 Oct 4:121:561-577. doi: 10.1016/j.ejmech.2016.05.065.
Takashi Nishiyama 1,  Noriyuki Hatae 2,  Teruki Yoshimura 2,  Sawa Takaki 1,  Takumi Abe 2,  Minoru Ishikura 2,  Satoshi Hibino 1,  Tominari Choshi 3
Affiliations

Affiliations

  • 1 Graduate School of Pharmacy Pharmaceutical Sciences, Faculty of Pharmacy and Pharmaceutical Sciences, Fukuyama University, Fukuyama, Hiroshima 729-0292, Japan.
  • 2 Faculty of Pharmaceutical Sciences, Health Sciences University of Hokkaido, Ishikari-Tobetsu, Hokkaido 061-0293, Japan.
  • 3 Graduate School of Pharmacy Pharmaceutical Sciences, Faculty of Pharmacy and Pharmaceutical Sciences, Fukuyama University, Fukuyama, Hiroshima 729-0292, Japan. Electronic address: choshi@fupharm.fukuyama-u.ac.jp.
PMID: 27318980 DOI: 10.1016/j.ejmech.2016.05.065
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.

Keywords

Antiproliferative activity; Carbazole-1,4-quinone; Koeniginequinone A; Koeniginequinone B.

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