494-56-4Relevant academic research and scientific papers
Toward establishing structure-activity relationships for oxygenated coumarins as differentiation inducers of promonocytic leukemic cells
Riveiro, Maria E.,Maes, Dominick,Vazquez, Ramiro,Vermeulen, Monica,Mangelinckx, Sven,Jacobs, Jan,Debenedetti, Silvia,Shayo, Carina,De Kimpe, Norbert,Davio, Carlos
scheme or table, p. 6547 - 6559 (2009/12/09)
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.
Two-photon uncaging with fluorescence reporting: Evaluation of the o-hydroxycinnamic platform
Gagey, Nathalie,Neveu, Pierre,Benbrahim, Chouaha,Goetz, Bernard,Aujard, Isabelle,Baudin, Jean-Bernard,Jullien, Ludovic
, p. 9986 - 9998 (2008/02/12)
This paper evaluates the ohydroxycinnamic platform for designing efficient caging groups with fluorescence reporting upon one- and two-photon excitation. The model cinnamates are easily prepared in one step by coupling commercial or readily available synthons. They exhibit a large one-photon absorption that can be tuned in the near-UV range. Uncaging after one-photon excitation was investigated by 1H NMR, UV-vis absorption, and steady-state fluorescence emission. In the whole investigated series, the caged substrate is quantitatively released upon photolysis. At the same time, uncaging releases a strongly fluorescent coproduct that can be used as a reporter for quantitative substrate delivery. The quantum yield of double bond photoisomerization leading to uncaging after one-photon absorption mostly lies in the 10% range. Taking advantage of the favorable photophysical properties of the uncaging coproduct, we use a series of techniques based on fluorescence emission to measure the action uncaging cross sections with two-photon excitation of the present cinnamates. Exhibiting values in the 1-10 GM range at 750 nm, they satisfactorily compare with the most efficient caging groups reported to date. Noticeably, the uncaging behavior with two-photon excitation is retained in vivo as suggested by the results observed in living zebrafish embryos. Reliable structure property relationships were extracted from analysis of the present collected data. In particular, the careful kinetic analysis allows us to discuss the relevance of the ohydroxycinnamic platform for diverse caging applications with one- and two-photon excitation.
Synthesis and structural revision of naturally occurring ayapin derivatives
Maes, Dominick,Vervisch, Stijn,Debenedetti, Silvia,Davio, Carlos,Mangelinckx, Sven,Giubellina, Nicola,De Kimpe, Norbert
, p. 2505 - 2511 (2007/10/03)
The synthesis of three highly oxygenated naturally occurring coumarins, 8-methoxy-6,7-methylenedioxycoumarin, 5-methoxy-6,7-methylenedioxycoumarin and 5,8-dimethoxy-6,7-methylenedioxycoumarin is described for the first time, together with a new method for the preparation of ayapin (6,7- methylenedioxycoumarin). Comparison of the spectroscopic data of the synthetic tetraoxygenated coumarin 5,8-dimethoxy-6,7-methylenedioxycoumarin with literature reports resulted in the structural revision of several natural coumarins. Two coumarins, both identified as 5,8-dimethoxy-6,7- methylenedioxycoumarin must have other structures, while the structure of another coumarin, described as the isomeric 7,8-dimethoxy-5,6- methylenedioxycoumarin has to be revised to 5,8-dimethoxy-6,7- methylenedioxycoumarin.
PROCESS FOR PREPARATION OF ESCULETIN COMPOUNDS, ESCULETIN COMPOUNDS AND INTERMEDIATES THEREOF, AND USE OF BOTH
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Page/Page column 11, (2010/01/31)
An esculetin compound, an intermediate thereof, a process for manufacturing an esculetin compound, and an antifungal composition for agriculture and horticulture and an herbicide comprising an esculetin compound or an intermediate thereof are provided. The process for manufacturing an esculetin compound is a low-cost, high-yield, and industrially practicable process, and comprises the following step.A process for manufacturing an esculetin compound of the formula (2): characterized by cyclizing a trihydroxybenzaldehyde compound of the formula (1): in an aprotic polar solvent in the presence of a weak base, with acetic anhydride or the like.
A Convenient & Short Route for the Synthesis of Ayapin & Scoparone
Kelkar, Shriniwas L.,Phadke, Chetan P.,Marina, Sister
, p. 458 - 459 (2007/10/02)
A short, convenient and general route to synthesise two important intermediates in coumarin synthesis, viz. 2-hydroxy-4,5-methylenedioxybenzaldehyde (4a) and 2-hydroxy-4,5-dimethoxybenzaldehyde (4b), is described.These have been converted by Wittig reaction into the naturally occurring coumarins, ayapin (1a) and scoparone (1b), respectively.
