Journal
BIOORGANIC & MEDICINAL CHEMISTRY
Volume 18, Issue 4, Pages 1610-1616Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.bmc.2009.12.073
Keywords
Naphthoquinone; Pterocarpan; Catalytic oxa-Heck reaction; Cancer; TNF-alpha modulation; Bioreduction
Funding
- FINEP
- Programa de Oncobiologia-UFRJ
- PRONEX
- FAPERJ
- CNPq
- CAPES
- FAF/FECD
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A new pterocarpanquinone (5a) was synthesized through a palladium catalyzed oxyarylation reaction and was transformed, through electrophilic substitution reaction, into derivatives 5b-d. These compounds showed to be active against human leukemic cell lines and human lung cancer cell lines. Even multidrug resistant cells were sensitive to 5a, which presented low toxicity toward peripheral blood mononuclear cells (PBMC) cells and decreased the production of TNF-alpha by these cells. In the laboratory these pterocarpanquinones were reduced by sodium dithionite in the presence of thiophenol at physiological pH, as NAD(P) H quinone oxidoredutase-1 (NQO1) catalyzed two-electron reduction, and the resulting hydroquinone undergo structural rearrangements, leading to the formation of Michael acceptors, which were intercepted as adducts of thiophenol. These results suggest that these compounds could be activated by bioreduction. (C) 2010 Elsevier Ltd. All rights reserved.
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