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Synthesis and Biological Evaluation of 2,5-Bis(alkylamino)-1,4-benzoquinones
Department of Chemistry, Federal University of Viçosa. Av. P.H. Rolfs, CEP 36570-000, Viçosa, MG, Brazil
Department of Physiology and Pharmacology, Federal University of Ceará, St. Coronel Nunes de Melo, 1127, CEP 60431-970, Fortaleza, CE, Brazil
* Author to whom correspondence should be addressed.
Received: 14 June 2010; in revised form: 14 July 2010 / Accepted: 16 July 2010 / Published: 13 August 2010
Abstract: A series of twelve 2,5-bis(alkylamino)-1,4-benzoquinones were prepared in yields ranging from 9–58% via the reaction between p-benzoquinone and various amines. The structures of the synthesized compounds were confirmed by IR, 1H- and 13C-NMR and MS analyses. The phytotoxicity of the 2,5-bis(alkylamino)-1,4-benzoquinones was evaluated against two crop species, Cucumis sativus and Sorgum bicolor, at 1.0 × 10-3 mol/L. In general, the quinones displayed inhibitory effects on the dicotyledonous species C. sativus (7–74%). On the other hand stimulatory effects were observed on S. bicolor (monocotyledonous). Similar results were observed in the biological assays carried out with the weed species Ipomoea grandifolia (dicotyledonous) and Brachiaria decumbens (monocotyledonous). In addition, the cytotoxicity of the 2,5-bis(alkylamino)-1,4-benzoquinones was assayed against HL-60 (leukemia), MDA-MB-435 (melanoma), SF-295 (brain) and HCT-8 (colon) human cancer cell lines and human peripheral blood mononuclear cells (PBMC), as representatives of healthy cells, using a MTT and an Alamar Blue assay. Compound 12 was the most active, displaying cytotoxicity against all cancer cell lines tested.
Keywords: quinones; herbicide; cytotoxicity
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Almeida Barbosa, L.C.; Alves Pereira, U.; Alvares Maltha, C.R.; Ricardo Teixeira, R.; Moreira Valente, V.M.; Oliveira Ferreira, J.R.; Costa-Lotufo, L.V.; Odorico Moraes, M.; Pessoa, C. Synthesis and Biological Evaluation of 2,5-Bis(alkylamino)-1,4-benzoquinones. Molecules 2010, 15, 5629-5643.
Almeida Barbosa LC, Alves Pereira U, Alvares Maltha CR, Ricardo Teixeira R, Moreira Valente VM, Oliveira Ferreira JR, Costa-Lotufo LV, Odorico Moraes M, Pessoa C. Synthesis and Biological Evaluation of 2,5-Bis(alkylamino)-1,4-benzoquinones. Molecules. 2010; 15(8):5629-5643.
Almeida Barbosa, Luiz Cláudio; Alves Pereira, Ulisses; Alvares Maltha, Célia Regina; Ricardo Teixeira, Róbson; Moreira Valente, Vânia Maria; Oliveira Ferreira, José Roberto; Costa-Lotufo, Letícia Veras; Odorico Moraes, Manoel; Pessoa, Cláudia. 2010. "Synthesis and Biological Evaluation of 2,5-Bis(alkylamino)-1,4-benzoquinones." Molecules 15, no. 8: 5629-5643.