Synthesis and cytotoxic activity of benzopyranoxanthone analogues of benz.
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.
Sittisombut
C
C
Laboratoire de Pharmacognosie de l'Université René Descartes, UMR/CNRS, Faculté des Sciences Pharmaceutiques et Biologiques, Paris, France.
Costes
N
N
Michel
S
S
Koch
M
M
Tillequin
F
F
Pfeiffer
B
B
Renard
P
P
Pierré
A
A
Atassi
G
G
D000818:Animals; D000970:Antineoplastic Agents / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology; D001580:Benzopyrenes / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology; D002455:Cell Division / Q000187:drug effects; D007939:Leukemia L1210 / Q000473:pathology; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D051379:Mice; D014407:Tumor Cells, Cultured
D000970:Antineoplastic Agents; D001580:Benzopyrenes