New Synthetic Procedure for 2-Aryl-1,4-naphthoquinone-1-oxime Methyl Ethers with Potent Antitumor Activity

Abstract 1,4-Naphthoquinone 1-oxime methyl ethers carrying an ester-substituted aryl pendant at 2-position were concisely prepared as seed compounds with structural flexibility for structure–activity relationship studies on antitumor activity. The key synthetic intermediate was a phthalide–tetralone...

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Bibliographic Details
Published in:Synlett 2014-09, Vol.25 (14), p.2059-2063
Main Authors: Mkhize, Scebi, Suzuki, Noriyuki, Kurosawa, Ayako, Fujinami, Makiko, Chaicharoenpong, Chanya, Ishikawa, Tsutomu
Format: Article
Language:English
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Summary:Abstract 1,4-Naphthoquinone 1-oxime methyl ethers carrying an ester-substituted aryl pendant at 2-position were concisely prepared as seed compounds with structural flexibility for structure–activity relationship studies on antitumor activity. The key synthetic intermediate was a phthalide–tetralone spiro compound, which was provided by palladium-coupling reaction between 2-bromobenzoate and 1-tetralone followed by OsO 4 –NMO oxidation.
ISSN:0936-5214
1437-2096
DOI:10.1055/s-0034-1378342