1. 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.
- Author
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Baiju TV, Almeida RG, Sivanandan ST, de Simone CA, Brito LM, Cavalcanti BC, Pessoa C, Namboothiri INN, and da Silva Júnior EN
- Subjects
- Acetates chemical synthesis, Acetates chemistry, Alkenes chemical synthesis, Alkenes chemistry, Amination, Antineoplastic Agents chemical synthesis, Cell Line, Tumor, Chemistry Techniques, Synthetic, Furans chemical synthesis, Furans chemistry, Furans pharmacology, Halogenation, Humans, Models, Molecular, Naphthoquinones chemical synthesis, Naphthoquinones chemistry, Neoplasms drug therapy, Pyrroles chemical synthesis, Quinones chemical synthesis, Structure-Activity Relationship, Antineoplastic Agents chemistry, Antineoplastic Agents pharmacology, Pyrroles chemistry, Pyrroles pharmacology, Quinones chemistry, Quinones pharmacology
- Abstract
Morita-Baylis-Hillman acetates and α-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 IC
50 values as low as < 2 μM. 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., (Copyright © 2018 Elsevier Masson SAS. All rights reserved.)- Published
- 2018
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