title: Synthesis and biological evaluation of 2,5-bis(alkylamino)-1,4-benzoquinones.
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 x 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.
authors: Department of Chemistry, Federal University of Viçosa. Av. P.H. Rolfs, Viçosa, MG, Brazil. lcab@ufv.br
authors: Luiz Cláudio Almeida
authors: LC
authors: Barbosa
authors: Ulisses Alves
authors: UA
authors: Pereira
authors: Célia Regina Alvares
authors: CR
authors: Maltha
authors: Róbson Ricardo
authors: RR
authors: Teixeira
authors: Vânia Maria
authors: VM
authors: Moreira Valente
authors: José Roberto
authors: JR
authors: Oliveira Ferreira
authors: Letícia Veras
authors: LV
authors: Costa-Lotufo
authors: Manoel Odorico
authors: MO
authors: Moraes
authors: Cláudia
authors: C
authors: Pessoa
mesh_terms: D000255:Adenosine Triphosphate / Q000378:metabolism; D000970:Antineoplastic Agents / Q000494:pharmacology; D016227:Benzoquinones / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D001681:Biological Assay; D016923:Cell Death / Q000187:drug effects; D045744:Cell Line, Tumor; D006801:Humans; D018517:Plant Roots / Q000187:drug effects / Q000254:growth & development
chemical_list: D000970:Antineoplastic Agents; D016227:Benzoquinones; D000255:Adenosine Triphosphate