Synthesis and biological evaluation of 2,5-bis(alkylamino)-1,4-benzoquinones.
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.
Barbosa
Luiz Cláudio Almeida
LC
Department of Chemistry, Federal University of Viçosa. Av. P.H. Rolfs, Viçosa, MG, Brazil. lcab@ufv.br
Pereira
Ulisses Alves
UA
Maltha
Célia Regina Alvares
CR
Teixeira
Róbson Ricardo
RR
Moreira Valente
Vânia Maria
VM
Oliveira Ferreira
José Roberto
JR
Costa-Lotufo
Letícia Veras
LV
Moraes
Manoel Odorico
MO
Pessoa
Cláudia
C
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
D000970:Antineoplastic Agents; D016227:Benzoquinones; D000255:Adenosine Triphosphate