期刊
BIOORGANIC & MEDICINAL CHEMISTRY
卷 19, 期 3, 页码 1264-1267出版社
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.bmc.2010.12.012
关键词
Isofuranonaphthoquinone; Ortho-lithiation; Anticancer activity; Siderophore
The first synthesis of 7,8-dihydroxy-1-methylnaphtho[2,3-c]furan-4,9-dione (1), an isofuranonaphthoquinone produced by an Actinoplanes strain is described. Lactone ring opening of 6-methylfuro [3,4-c]furan-1(3H)-one (4) with ortho-lithiated veratrole (3), oxidation of product alcohol 5, and Friedel-Crafts acylation of the resulting aroylcarboxylic acid 7 afforded the mono methyl ether 2 of the target compound. The latter was obtained by demethylation of 2 with BBr3 in 14% overall yield. While mono ether 2 was distinctly more cytotoxic than catechol 1 against a panel of five cancer cell lines, only the latter showed a siderophore-like binding affinity for Fe(III) with a complex dissociation constant K-D of approximately 10(-29) M-3 (pM = 25.9). (C) 2010 Elsevier Ltd. All rights reserved.
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