Cascade synthesis of polyoxygenated 6H,11H-[2]benzopyrano-[4,3-c][1]benzopyran-11-ones.
2-(methoxymethoxymethyl)aryllead triacetates, obtained in situ from the corresponding arylboronic acids, reacted with 4-hydroxycoumarins, leading to 3-(2-methoxymethoxymethyl)aryl-4-hydroxycoumarin derivatives in good to high yields. These compounds underwent a cascade sequence of reactions, deprotection-halogenation-annulation, to afford polyoxygenated tetracyclic 6H,11H-[2]benzopyrano-[4,3-c] [1]benzopyran-11-ones in good yields. Some compounds showed a moderate cytotoxicity against human epithelial mammary HBL100 cells.
Naumov
Mikael I
MI
Department of Chemistry, Nizhnyi Novgorod N. I. Lobachevsky State University, 23 Gagarin Avenue, 603950 Nizhnyi Novgorod, Russia.
Sutirin
Sergey A
SA
Shavyrin
Andrey S
AS
Ganina
Olga G
OG
Beletskaya
Irina P
IP
Bourgarel-Rey
Véronique
V
Combes
Sébastien
S
Finet
Jean-Pierre
JP
Fedorov
Alexey Yu
AY
D015110:4-Hydroxycoumarins / Q000737:chemistry; D000970:Antineoplastic Agents / Q000737:chemistry / Q000494:pharmacology; D001578:Benzopyrans / Q000737:chemistry* / Q000494:pharmacology; D001880:Boranes / Q000737:chemistry; D002478:Cells, Cultured; D002625:Chemistry, Organic / Q000379:methods*; D004354:Drug Screening Assays, Antitumor; D004847:Epithelial Cells; D006801:Humans; D010100:Oxygen / Q000737:chemistry; D018675:Toxicity Tests
D015110:4-Hydroxycoumarins; D000970:Antineoplastic Agents; D001578:Benzopyrans; D001880:Boranes; D010100:Oxygen; C068805:4-hydroxycoumarin