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2005
Benzopyran derivatives
R 0350
Synthesis of 4-Hydroxycoumarin and 2,4-Quinolinediol Derivatives and Evaluaof Their Effects on the Viability of HepG2 Cells ad Human Hepatocytes Cul11- 148 tion
ture. — The synthesis of benzothiazine derivatives (III) of coumarins and quinolones
(I) proceeds via a nonisolable enaminone intermediate by an intramolecular cyclization. Benzylidenecoumarins and -quinolones (V) are prepared by Knoevenagel condensation of hydroxycoumarins and quinolinediols (Ia)—(Ic) with benzaldehydes (IV).
The presence of a heterocycle with nitrogen and sulfur heteroatoms on the quinolone
or benzopyrone system or a benzylidene at the 3-position is essential for the protective
effect of these compounds against tert-butyl hydroperoxide(t-BHP)-induced decrease
in viability of cells. Coumarin (IIIc) is particularly interesting for its protective activity
against t-BHP-induced cytotoxicity in the cultured human hepatoma HepG2 cell line.
— (REFOUVELET*, B.; et al.; Eur. J. Med. Chem. 39 (2004) 11, 931-937; Lab.
Chim. Org. Ther., Fac. Med. Pharm., Univ. Franche-Comte, F-25030 Besancon, Fr.;
Eng.) — H. Hoennerscheid
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