ChemInform Abstract: Synthesis and Cytotoxic Activity of Benzopyranoxanthone Analogues of Benzo[b]acronycine and Psorospermine

Autor: Francois Tillequin, Alain Pierre, Michel H. J. Koch, Sylvie Michel, Nadine Costes, Chavalit Sittisombut, Bruno Pfeiffer, Ghanem Atassi, Pierre Renard
Rok vydání: 2010
Předmět:
Zdroj: ChemInform. 32
ISSN: 1522-2667
0931-7597
Popis: Condensation of 3-hydroxy-2-naphthalenecarboxylic acid with phloroglucinol afforded 1,3-dihydroxy-12H-benzo[b]xanthen-12-one. Construction of an additional dimethylpyran ring onto this skeleton, by alkylation with 3-chloro-3-methyl-1-butyne followed by Claisen rearrangement, gave access to a series of benzo[b]pyrano[2,3-i]xanthen-6-ones and benzo[b]pyrano[3,2-h]xanthen-7-ones related to psorospermine and benzo[b]acronycine. In contrast with what is observed in the pyridoacridone and benzopyridoacridone series, the linear benzo[b]-pyrano[2,3-i]xanthen-6-one derivatives were more potent than their angular benzo[b]pyrano[3,2-h]xanthen-7-one isomers. cis-3,4-Diacetoxy-5-methoxy-2,2-dimethyl-3,4-dihydro-2H,6H-benzo[b]pyrano[2,3-i]xanthen-6-one, the most active among the new compounds, was more potent than acronycine in inhibiting the proliferation of L1210 murine leukemia cells.
Databáze: OpenAIRE
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