Concise synthesis and antiproliferative activity evaluation of ellipticine quinone and its analogs

被引：18

作者：

Nishiyama, Takashi ^{[1
]}

Hatae, Noriyuki ^{[2
]}

Mizutani, Masataka ^{[2
]}

Yoshimura, Teruki ^{[2
]}

Kitamura, Tsuyoshi ^{[1
]}

Miyano, Mana ^{[1
]}

Fujii, Mami ^{[1
]}

Satsuki, Nanase ^{[1
]}

Ishikura, Minoru ^{[2
]}

Hibino, Satoshi ^{[1
]}

Choshi, Tominari ^{[1
]}

机构：

[1] Fukuyama Univ, Grad Sch Pharm Pharmaceut Sci, Fac Pharm & Pharmaceut Sci, Fukuyama, Hiroshima 7290292, Japan

[2] Hlth Sci Univ Hokkaido, Fac Pharmaceut Sci, Ishikari, Hokkaido 0610293, Japan

来源：

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY | 2017年 / 136卷

关键词：

Carbazole-1,4-quinone; Ring-Closing Metathesis; Pyrido[4,3-b]carbozole-5,11-quinone; Ellipticine quinone; Antiproliferative activity; CELL-PROTECTING SUBSTANCE; CALOTHRIXIN-B; MURRAYAQUINONE-A; STREPTOMYCES-EXFOLIATUS; CARBAZOLE ALKALOIDS; EFFICIENT SYNTHESIS; FORMAL SYNTHESIS; CARQUINOSTATIN; DERIVATIVES; METATHESIS;

D O I：

10.1016/j.ejmech.2017.04.071

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

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. (C) 2017 Elsevier Masson SAS. All rights reserved.

引用

页码：1 / 13

页数：13

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