Quinonoid compounds via reactions of lawsone and 2-aminonaphthoquinone with α-bromonitroalkenes and nitroallylic acetates: Structural diversity by C-ring modification and cytotoxic evaluation against cancer cells

被引：51

作者：

Baiju, Thekke V. ^{[1
]}

Almeida, Renata G. ^{[2
]}

Sivanandan, Sudheesh T. ^{[1
]}

de Simone, Carlos A. ^{[3
]}

Brito, Lucas M. ^{[4
]}

Cavalcanti, Bruno C. ^{[4
]}

Pessoa, Claudia ^{[4
]}

Namboothiri, Irishi N. N. ^{[1
]}

da Silva Junior, Eufranio N. ^{[2
]}

机构：

[1] Indian Inst Technol, Dept Chem, Bombay 400076, Maharashtra, India

[2] Univ Fed Minas Gerais, Dept Chem, Inst Exact Sci, BR-31270901 Belo Horizonte, MG, Brazil

[3] Univ Sao Paulo, Inst Phys, Dept Phys & Informat, BR-13560160 Sao Carlos, SP, Brazil

[4] Univ Fed Ceara, Dept Physiol & Pharmacol, BR-60180900 Fortaleza, Ceara, Brazil

来源：

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY | 2018年 / 151卷

关键词：

MORITA-BAYLIS-HILLMAN; FREE-RADICAL REACTIONS; CATALYZED INTRAMOLECULAR CYCLIZATION; HIGHLY ENANTIOSELECTIVE SYNTHESIS; CASCADE REACTIONS; 1,4-NAPHTHOQUINONE DERIVATIVES; ASYMMETRIC-SYNTHESIS; ANTITUMOR-ACTIVITY; NAPHTHOQUINONE DERIVATIVES; CONJUGATED NITROALKENES;

D O I：

10.1016/j.ejmech.2018.03.079

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

Morita-Baylis-Hillman acetates and alpha-bromonitroalkenes have been employed in cascade reactions with lawsone and 2-aminonaphthoquinone for the one-pot synthesis of heterocycle fused quinonoid compounds. The reactions reported here utilized the 1,3-binucleophilic potential of hydroxy- and aminonaphthoquinones and the 1,2/1,3-bielectrophilic potential of bromonitroalkenes and Morita-Baylis Hillman acetates for the synthesis of pyrrole and furan fused naphthoquinones. The synthesized compounds were evaluated against HCT-116 (human colon carcinoma cells), PC3 (human prostate cancer cells), HL-60 (human promyelocytic leukemia cells), SF295 (human glioblastoma cells) and NCI-H460 (human lung cancer cells) and exhibited antitumor activity with IC50 values as low as < 2 mu M. Selected compounds were also evaluated against OVCAR-8 (ovary), MX-1 (breast) and JURKAT (leukemia) cell lines. The cytotoxic potential of the quinones evaluated was also assayed using non-tumor cells, exemplified by peripheral blood mononuclear (PBMC) and L929 cells. (C) 2018 Elsevier Masson SAS. All rights reserved.

引用

页码：686 / 704

页数：19

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