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

共 57 条

[1] [Anonymous], 1990, ADV HETEROCYCLIC NAT
[2] Regioselective intramolecular reactions of 2-indolylacyl radicals with pyridines: A direct synthetic entry to ellipticine quinones
Bennasar, ML
Roca, T
Ferrando, F
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (22) : 9077 - 9080
[3] Synthesis, electrochemistry, and bioactivity of the cyanobacterial calothrixins and related quinones
Bernardo, PH
Chai, CLL
Heath, GA
Mahon, PJ
Smith, GD
Waring, P
Wilkes, BA
[J]. JOURNAL OF MEDICINAL CHEMISTRY, 2004, 47 (20) : 4958 - 4963
[4] Charra M., 1991, J BIOL CHEM, V25, P1820
[5] Total syntheses of carazostatin, hyellazole, and carbazoquinocins B-F
Choshi, T
Sada, T
Fujimoto, H
Nagayama, C
Sugino, E
Hibino, S
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (08) : 2535 - 2543
[6] Total syntheses of carazostatin and hyellazole by allene-mediated electrocyclic reaction
Choshi, T
Sada, T
Fujimoto, H
Nagayama, C
Sugino, E
Hibino, S
[J]. TETRAHEDRON LETTERS, 1996, 37 (15) : 2593 - 2596
[7] Lipase-catalyzed asymmetric synthesis of desprenyl-carquinostatin A and descycloavandulyl-lavanduquinocin
Choshi, Tominari
Uchida, Yoshinari
Kubota, Yukiko
Nobuhiro, Junko
Takeshita, Mitsuhiro
Hatano, Takushi
Hibino, Satoshi
[J]. CHEMICAL & PHARMACEUTICAL BULLETIN, 2007, 55 (07) : 1060 - 1064
[8] PROGRESS TOWARDS THE TOTAL SYNTHESIS OF THE BIOACTIVE CALOTHRIXINS A AND B
Choshi, Tominari
Hibino, Satoshi
[J]. HETEROCYCLES, 2009, 77 (01) : 85 - 97
[9] ELLIPTICINE INCREASES THE SUPERHELICAL DENSITY OF INTRACELLULAR SV40-DNA BY INTERCALATION
CHU, Y
HSU, MT
[J]. NUCLEIC ACIDS RESEARCH, 1992, 20 (15) : 4033 - 4038
[10] Olerin metathesis of amine-containing systems: Beyond the current consensus
Compain, Philippe
[J]. ADVANCED SYNTHESIS & CATALYSIS, 2007, 349 (11-12) : 1829 - 1846

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