1. Concise synthesis and antiproliferative activity evaluation of ellipticine quinone and its analogs.
- Author
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Nishiyama, Takashi, Hatae, Noriyuki, Mizutani, Masataka, Yoshimura, Teruki, Kitamura, Tsuyoshi, Miyano, Mana, Fujii, Mami, Satsuki, Nanase, Ishikura, Minoru, Hibino, Satoshi, and Choshi, Tominari
- Subjects
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CHEMICAL synthesis , *QUINONE , *DEHYDROGENATION , *METATHESIS reactions , *CARBAZOLE - Abstract
We developed a concise protocol for the synthesis of ellipticine quinone from the appropriate 3-iodoindole-2-carbaldehydes in four steps. The key step is the construction of carbazole-1,4-quinone through tandem Ring-Closing Metathesis (RCM) and dehydrogenation under oxygen atmosphere. Therefore, the ellipticine quinone analogs possessing substitution at the 8- and/or 9-positions were synthesized using this method. In total, 14 compounds were evaluated for antiproliferative activity against HCT-116 and HL-60 cell lines; 9-nitroellipticine quinone was found to have superior activity compared to calothrixin B. [ABSTRACT FROM AUTHOR]
- Published
- 2017
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