- Toward establishing structure-activity relationships for oxygenated coumarins as differentiation inducers of promonocytic leukemic cells
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The presumption that some coumarins might be lead compounds in the search for new differentiation agents against leukemia is based on the fact that natural coumarins, 5-(3-methyl-2-butenyloxy)-6,7-methylenedioxycoumarin (C-2) and 5-methoxy-6,7-methylenedioxycoumarin (C-1) inhibit proliferation and induce differentiation in U-937 cells [Riveiro, M. E.; Shayo, C.; Monczor, F.; Fernandez, N.; Baldi, A.; De Kimpe, N.; Rossi, J.; Debenedetti, S.; Davio, C. Cancer Lett. 2004, 210, 179-188]. These promising findings prompted us to investigate the anti-leukemia activity of a broader range of related polyoxygenated coumarins. Twenty related natural or synthetically prepared coumarins, including a range of 5-substituted ayapin derivatives which have become easy accessible via newly developed synthesis methods, were evaluated, where treatments with 5-(2,3-dihydroxy-3-methylbutoxy)-6,7-methylenedioxycoumarin (D-3) and 5-(2-hydroxy-3-methoxy-3-methylbutoxy)-6,7-methylenedioxycoumarin (D-2) were able to inhibit the cell growth and induce the differentiation of U-937 cells after 48 h treatment. These results provide insight into the correlation between some structural properties of polyoxygenated coumarins and their in vitro leukemic differentiation activity.
- Riveiro, Maria E.,Maes, Dominick,Vazquez, Ramiro,Vermeulen, Monica,Mangelinckx, Sven,Jacobs, Jan,Debenedetti, Silvia,Shayo, Carina,De Kimpe, Norbert,Davio, Carlos
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scheme or table
p. 6547 - 6559
(2009/12/09)
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- Total synthesis of naturally occurring 5,6,7- and 5,7,8-trioxygenated coumarins
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The synthesis of five naturally occurring polyoxygenated coumarins is described. It concerns two 5,6,7-trioxygenated coumarins, i.e., 6-hydroxy-5,7-dimethoxycoumarin (fraxinol) 1 and 5,6,7-trimethoxycoumarin 2, and three 5,7,8-trioxygenated coumarins, i.e., 8-hydroxy-5,7-dimethoxycoumarin (leptodactylone) 3, 5,7,8-trimethoxycoumarin 4 and 8-(3-methyl-2-butenyloxy)-5,7-dimethoxycoumarin (artanin) 5. Key feature of the synthetic pathway is the synthesis of suitable tetraoxygenated benzaldehydes, which are then converted to the corresponding coumarins via a Wittig reaction.
- Maes, Dominick,Riveiro, Maria Eugenia,Shayo, Carina,Davio, Carlos,Debenedetti, Silvia,De Kimpe, Norbert
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p. 4438 - 4443
(2008/09/21)
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- Toddalenone: A new coumarin from Toddalia asiatica (T. Aculeata). Structural establishment based on the chemical conversion of limettin into toddalenone
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Toddalenone, a new coumarin, was isolated from Toddalia asiatica (L.) Lam. (T. aculeata Pers.). Its structure was established as the formula (1) by correlation with limettin (2). Vilsmeir-Haack formylation of limettin (2) gave 8-formyllimettin (10) in good yield. Aldol condensation of this material (10) with acetone afforded toddalenone (1).
- Ishii,Kobayashi,Ishikawa
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p. 3330 - 3333
(2007/10/02)
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