Synthesis and Biological Evaluation of 2,5-Bis(alkylamino)-1,4-benzoquinones

doi:10.3390/molecules15085629

This article is

freely available
re-usable

Molecules 2010, 15(8), 5629-5643; doi:10.3390/molecules15085629

Article

Synthesis and Biological Evaluation of 2,5-Bis(alkylamino)-1,4-benzoquinones

Luiz Cláudio Almeida Barbosa^1,* , Ulisses Alves Pereira¹, Célia Regina Alvares Maltha¹, Róbson Ricardo Teixeira¹, Vânia Maria Moreira Valente¹, José Roberto Oliveira Ferreira², Letícia Veras Costa-Lotufo², Manoel Odorico Moraes² and Cláudia Pessoa²

¹ Department of Chemistry, Federal University of Viçosa. Av. P.H. Rolfs, CEP 36570-000, Viçosa, MG, Brazil ² 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

Download PDF Full-Text [169 KB, uploaded 13 August 2010 14:03 CEST]

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

Article Statistics

Click here to load and display the download statistics.

Cite This Article

MDPI and ACS Style

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.

AMA Style

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(8):5629-5643.

Chicago/Turabian Style

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.

Molecules EISSN 1420-3049 Published by MDPI Publishing, Basel, Switzerland RSS E-Mail Table of Contents Alert