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

Molecules

Luiz Cláudio Almeida Barbosa¹  Ulisses Alves Pereira¹  Célia Regina Alvares Maltha¹  Róbson Ricardo Teixeira¹  Vânia Maria Moreira Valente¹  José Roberto Oliveira Ferreira¹  Letícia Veras Costa-Lotufo¹  Manoel Odorico Moraes¹ 

[1] ¹Department of Chemistry, Federal University of Viçosa. Av. P.H. Rolfs, CEP 36570-000, Viçosa, MG, Brazil ²Department of Physiology and Pharmacology, Federal University of Ceará, St. Coronel Nunes de Melo, 1127, CEP 60431-970, Fortaleza, CE, Brazil

关键词: quinones;    herbicide;    cytotoxicity;   

DOI  :  10.3390/molecules15085629

来源: mdpi

【 摘 要 】

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.

【 授权许可】

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