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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.
AuthorsLuiz Cláudio Almeida Barbosa, Ulisses Alves Pereira, Célia Regina Alvares Maltha, Róbson Ricardo Teixeira, Vânia Maria Moreira Valente, José Roberto Oliveira Ferreira, Letícia Veras Costa-Lotufo, Manoel Odorico Moraes, Cláudia Pessoa
JournalMolecules (Basel, Switzerland) (Molecules) Vol. 15 Issue 8 Pg. 5629-43 (Aug 13 2010) ISSN: 1420-3049 [Electronic] Switzerland
PMID20714317 (Publication Type: Journal Article, Research Support, Non-U.S. Gov't)
Chemical References
  • Antineoplastic Agents
  • Benzoquinones
  • Adenosine Triphosphate
Topics
  • Adenosine Triphosphate (metabolism)
  • Antineoplastic Agents (pharmacology)
  • Benzoquinones (chemical synthesis, chemistry, pharmacology)
  • Biological Assay
  • Cell Death (drug effects)
  • Cell Line, Tumor
  • Humans
  • Plant Roots (drug effects, growth & development)

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